Synthesis of Fluorinated β-Amino
Acids

Koichi Mikami; Santos Fustero; Maria Sánchez-Roselló; José Luis Aceña; Vadim Soloshonok; Alexander Sorochinsky

doi:10.1055/s-0030-1260173

REVIEW

Synthesis of Fluorinated β-Amino Acids

Koichi Mikami^a, Santos Fustero^b,c, Maria Sánchez-Roselló^c, José Luis Aceña^c, Vadim Soloshonok^d,e, Alexander Sorochinsky*^f
^a Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Tokyo 152-8552, Japan
^b Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia, Spain
^c Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain
^d Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastian, Spain
^e IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain
^f Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street 1, 02660 Kyiv-94, Ukraine
Fax: +380(44)5732552; e-Mail: sorochinsky@bpci.kiev.ua;

Abstract

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Abstract

The major goal of this review is to provide an overview of the general synthetic methods available in the literature for preparing fluorinated β-amino acids and their derivatives. These compounds have been employed in combination with non-fluorinated amino acids in the design of peptides and peptidomimetics for investigation of their proteolytic stability and influence of molecular composition on the folding properties and biological activity. Fluorinated β-amino acids serve as precursors for the β-lactam antibiotics and fluoroalkene dipeptide isosteres or as structural components of analogues of natural products. There are several general methods available for introducing into β-amino acids either one or two fluorine atoms at the α-position, as well as α- or β-fluoroalkyl substituents; these methods include reduction of fluorinated β-imino esters, biomimetic transamination of fluorinated carbonyl compounds, Michael-type addition to trifluorocrotonate and α-trifluoromethacrylate derivatives, and Reformatsky and Mannich-type reactions of fluorinated substrates. Fluorinated aziridines and β-lactams have been employed as synthetic intermediates for the preparation of the corresponding β-amino acids by facile ring-opening reactions. Other methods discussed in review are fluorination and trifluoromethylation of β-amino acid derivatives, reactions of organometallic reagents with fluorinated imines and related compounds, and metathesis reactions of fluorinated imino esters and imidoyl halides for the synthesis of cyclic derivatives.

1 Introduction

2 Fluorination and Trifluoromethylation of β-Amino Acid Derivatives

3 Reduction of Fluorinated β-Imino Esters

4 Biomimetic Transamination of Fluorinated Carbonyl Compounds

5 Michael-Type Additions to β-Trifluorocrotonate and α-Trifluoromethacrylate Derivatives

6 Reformatsky-Type Reaction of Fluorinated Substrates

7 Mannich-Type Reactions of Fluorinated Substrates

8 Cycloaddition Reactions of Fluoroalkyl Imines

9 Reactions of Organometallic Reagents with Fluorinated Imines and Related Compounds

10 Metathesis Reactions

11 Miscellaneous Reactions

12 Conclusions

Key words

fluorine - β-amino acids - asymmetric synthesis - biomimetic synthesis - biologically active compounds - synthetic methodology

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Referenzen

References

<A NAME="RE61011SS-1A">1a</A> Frackenpohl J. Arvidsson PI. Schreiber JV. Seebach D. ChemBioChem 2001, 2: 445

<A NAME="RE61011SS-1B">1b</A> Cheng RP. Gellman SH. DeGrado WF. Chem. Rev. 2001, 101: 3219

<A NAME="RE61011SS-1C">1c</A> Hook DF. Gessier F. Noti C. Kast P. Seebach D. ChemBioChem 2004, 5: 691

<A NAME="RE61011SS-1D">1d</A> Mathad RI. Gessier F. Seebach D. Jaun B. Helv. Chim. Acta 2005, 88: 266

<A NAME="RE61011SS-1E">1e</A> Disney MD. Hook DF. Namoto K. Seeberger PH. Seebach D. Chemistry & Biodiversity 2005, 2: 1624

<A NAME="RE61011SS-1F">1f</A> Fülöp F. Martikek TA. Tóth GK. Chem. Soc. Rev. 2006, 35: 323

<A NAME="RE61011SS-1G">1g</A> Mathad RI. Jaun B. Flögel O. Gardiner J. Löweneck M. Codée JD. Seeberger PH. Seebach D. Edmonds MK. Graichen FH. Abell AD. Helv. Chim. Acta 2007, 90: 2251

<A NAME="RE61011SS-1H">1h</A> Wu YD. Han W. Wang DP. Zhao YL. Acc. Chem. Res. 2008, 41: 1418

<A NAME="RE61011SS-2A">2a</A> Seebach D. Namoto K. Mahajan YR. Bindschädler P. Sustmann R. Kirsch M. Ryder NS. Weiss M. Sauer M. Roth C. Werner S. Beer H.-D. Mundling C. Walde P. Voser M. Chemistry & Biodiversity 2004, 1: 65

<A NAME="RE61011SS-2B">2b</A> Rueping M. Mahajan YR. Sauer M. Seebach D. ChemBioChem 2002, 3: 257

<A NAME="RE61011SS-3">3</A> Seebach D. Gardiner J. Acc. Chem. Res. 2008, 41: 1366

<A NAME="RE61011SS-4A">4a</A> Porter EA. Wang X. Lee H.-S. Weisblum B. Gellman SH. Nature 2000, 404: 565

<A NAME="RE61011SS-4B">4b</A> Liu M. Sibi MP. Tetrahedron 2002, 58: 7991

<A NAME="RE61011SS-4C">4c</A> Arvidsson PI. Ryder NS. Weiss HM. Gross G. Kretz O. Woessner R. Seebach D. ChemBioChem 2003, 4: 1345

<A NAME="RE61011SS-4D">4d</A> Seebach D. Kimmerlin T. Sebesta R. Campo MA. Beck AK. Tetrahedron 2004, 60: 7455

<A NAME="RE61011SS-4E">4e</A> Bialy L. Waldmann H. Angew. Chem. Int. Ed. 2005, 44: 2

<A NAME="RE61011SS-4F">4f</A> Specker E. Bottcher J. Lilie H. Heine A. Schoop A. Muller G. Griebenow N. Klebe G. Angew. Chem. Int. Ed. 2005, 44: 3140

<A NAME="RE61011SS-4G">4g</A> Kuhl A. Hahn MG. Dumié M. Mittendorf J. Amino Acids 2005, 29: 89

<A NAME="RE61011SS-4H">4h</A> Isanbor Ch. O’Hagan D. J. Fluorine Chem. 2006, 127: 303

<A NAME="RE61011SS-4I">4i</A> Karlsson AJ. Pomerantz WC. Weisblum B. Gellman SH. Palecek SP. J. Am. Chem. Soc. 2006, 128: 12630

<A NAME="RE61011SS-4J">4j</A> Benedek G. Palkó M. Wéber E. Martinek TA. Forró E. Fülöp F. Eur. J. Org. Chem. 2008, 3724

<A NAME="RE61011SS-5A">5a</A> Seebach D. Overhand M. Kühnle FNM. Martinoni B. Oberer L. Hommel U. Widmer H. Helv. Chim. Acta 1996, 79: 913

<A NAME="RE61011SS-5B">5b</A> Seebach D. Beck AK. Bierbaum DJ. Chemistry & Biodivesity 2004, 1: 1111

<A NAME="RE61011SS-6">6</A> Appella DH. Christianson LA. Karle IL. Powell DR. Gellman SH. J. Am. Chem. Soc. 1996, 118: 13071

<A NAME="RE61011SS-7">7</A> Seebach D. Hook DF. Glättli A. Biopolymers (Peptide Sci.) 2006, 84: 23

<A NAME="RE61011SS-8A">8a</A> Raguse TL. Lai JR. LePlae PR. Gellman SH. Org. Lett. 2001, 3: 3963

<A NAME="RE61011SS-8B">8b</A> Glättli A. Seebach D. van Gunsteren WF. Helv. Chim. Acta 2004, 87: 2487

<A NAME="RE61011SS-9A">9a</A> Gessier F. Noti C. Rueping M. Seebach D. Helv. Chim. Acta 2003, 86: 1862

<A NAME="RE61011SS-9B">9b</A> Gattin Z. van Gunsteren WF. J. Phys. Chem. B 2009, 113: 8695

<A NAME="RE61011SS-9C">9c</A> Jaun B. Seebach D. Mathad RI. Helv. Chim. Acta 2011, 94: 335

<A NAME="RE61011SS-10A">10a</A> Colombo G. Malpezzi L. Mazzini S. Meille SV. Meli M. Ramirez de Arellano C. Zanda M. Chem. Eur. J. 2003, 9: 4510

<A NAME="RE61011SS-10B">10b</A> Zanda M. New J. Chem. 2004, 28: 1401

<A NAME="RE61011SS-11A">11a</A> Thaisrivongs S. Schostarez H. Pals DT. Turner SR. J. Med. Chem. 1987, 30: 1837

<A NAME="RE61011SS-11B">11b</A> Sergeeva NN. Golubev AS. Burger K. Synthesis 2001, 281

<A NAME="RE61011SS-11C">11c</A> Gouge V. Jubault P. Quirion J.-C. Tetrahedron Lett. 2004, 45: 773

<A NAME="RE61011SS-11D">11d</A> Li X.-G. Lähitie M. Kanerva LT. Tetrahedron: Asymmetry 2008, 19: 1857

<A NAME="RE61011SS-12A">12a</A> Ohba T. Ikeda E. Takei H. Bioorg. Med. Chem. Lett. 1996, 6: 1875

<A NAME="RE61011SS-12B">12b</A> Peddie V. Pietsch M. Bromfield KM. Pike RN. Duggan PJ. Abell AD. Synthesis 2010, 1845

<A NAME="RE61011SS-13A">13a</A> Hart DJ. Ha D.-C. Chem. Rev. 1989, 89: 1447

<A NAME="RE61011SS-13B">13b</A> van de Steen FH. van Koten G. Tetrahedron 1991, 47: 7503

<A NAME="RE61011SS-13C">13c</A> Benaglia M. Cinquini M. Cozzi F. Eur. J. Org. Chem. 2000, 563

<A NAME="RE61011SS-13D">13d</A> Lacroix S. Cheguillaume A. Gera S. Marchand-Brynaert . Synthesis 2003, 2483

<A NAME="RE61011SS-13E">13e</A> Bordeau M. Frebault F. G obet M. Picard J.-P. Eur. J. Org. Chem. 2006, 4147

<A NAME="RE61011SS-13F">13f</A> Mohar B. Stephan M. Urleb U. Tetrahedron 2010, 66: 4144

<A NAME="RE61011SS-14A">14a</A> Niida A. Tomita K. Mizumoto M. Tanigaki H. Terada T. Oishi S. Otaka A. Inui K. Fujii N. Org. Lett. 2006, 8: 613

<A NAME="RE61011SS-14B">14b</A> Narumi T. Niida A. Tomita K. Oishi S. Otaka A. Ohno H. Fujii N. Chem. Commun. 2006, 4720

<A NAME="RE61011SS-14C">14c</A> Narumi T. Tomita K. Inokuchi E. Kobayashi K. Oishi S. Ohno H. Fujii N. Tetrahedron 2008, 64: 4332

<A NAME="RE61011SS-14D">14d</A> Oishi S. Kamitani H. Kodera Y. Watanabe K. Kobayashi K. Narumi T. Tomita K. Ohno H. Naito T. Kodama E. Matsuoka M. Fujii N. Org. Biomol. Chem. 2009, 7: 2872

<A NAME="RE61011SS-15A">15a</A> Gong Y. Kato K. J. Fluorine Chem. 2001, 111: 77

<A NAME="RE61011SS-15B">15b</A> Gong Y. Kato K. J. Fluorine Chem. 2004, 125: 767

<A NAME="RE61011SS-16A">16a</A> Cheguillaume A. Lacroix S. Marchand-Brynaert J. Tetrahedron Lett. 2003, 44: 2375

<A NAME="RE61011SS-16B">16b</A> Cheguillaume A. Gillart J. Labar D. Grégoire V. Marchand-Brynaert J. Bioorg. Med. Chem. 2005, 13: 1357

<A NAME="RE61011SS-17">17</A> Nakayama K. Kawato HC. Inagaki H. Nakajima R. Kitamura A. Someya K. Ohta T. Org. Lett. 2000, 2: 977

<A NAME="RE61011SS-18A">18a</A> Uoto K. Ohsuki S. Takenoshita H. Ishiyama T. Iimura S. Hirota Y. Mitsui I. Hirofumi T. Soga T. Chem. Pharm. Bull. 1997, 45: 1793

<A NAME="RE61011SS-18B">18b</A> Ojima I. Slater JC. Perea P. Vieth JM. Abouabdellah A. Bégué J.-P. Bernacki RJ. Bioorg. Med. Chem. Lett. 1997, 7: 133

<A NAME="RE61011SS-18C">18c</A> Ojima I. Wang T. Miller M. Lin S. Borella CP. Pera P. Bernacki RJ. Bioorg. Med. Chem. Lett. 1999, 9: 3423

<A NAME="RE61011SS-18D">18d</A> Ojima I. Lin S. Slater JC. Wang T. Pera P. Bernacki RJ. Ferlini C. Scambia G. Bioorg. Med. Chem. 2000, 8: 1619

<A NAME="RE61011SS-18E">18e</A> Ojima I. Lin S. Wang T. Curr. Med. Chem. 1999, 6: 927

<A NAME="RE61011SS-18F">18f</A> Kuznetsova L. Ungureanu IM. Pepe A. Zanardi I. Wu X. Ojima I. J. Fluorine Chem. 2004, 125: 487

<A NAME="RE61011SS-19A">19a</A> Soloshonok VA. Curr. Org. Chem. 2002, 6: 341

<A NAME="RE61011SS-19B">19b</A> Qiu X.-L. Meng W.-D. Qing F.-L. Tetrahedron 2004, 60: 6711

<A NAME="RE61011SS-19C">19c</A> Bégué J.-P. Bonnet-Delpon D. Crousse B. Legros J. Chem. Soc. Rev. 2005, 34: 562

<A NAME="RE61011SS-19D">19d</A> Nie J. Guo H.-C. Cahard D. Ma J.-A. Chem. Rev. 2011, 111: 455

<A NAME="RE61011SS-20A">20a</A> Fluorine-containing Amino Acids: Synthesis and Properties Kukhar VP. Soloshonok VA. Wiley; Chichester: 1994.

<A NAME="RE61011SS-20B">20b</A> Enantiocontrolled Synthesis of Fluoro-organic Compounds Soloshonok VA. Wiley; Chichester: 1999.

<A NAME="RE61011SS-20C">20c</A> Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions Ramachandran PV. American Chemical Society; Washington DC: 2000.

<A NAME="RE61011SS-20D">20d</A> Fluorine in Medicinal Chemistry and Chemical Biology Ojima I. John Wiley & Sons; New Jersey: 2009.

<A NAME="RE61011SS-21A">21a</A> Fustero S. Sanz-Cervera JF. Soloshonok VA. In Enantioselective Synthesis of β-Amino Acids 2nd ed.: Juaristi EC. Soloshonok VA. Wiley-VCH; Weinheim: 2005. p.319

<A NAME="RE61011SS-21B">21b</A> Aceña JL. Simón-Fuentes A. Fustero S. Curr. Org. Chem. 2010, 14: 928

<A NAME="RE61011SS-21C">21c</A> Sorochinsky AE. Soloshonok VA. J. Fluorine Chem. 2010, 131: 127

<A NAME="RE61011SS-22">22</A> Singh RP. Shreeve JM. Synthesis 2002, 2561

<A NAME="RE61011SS-23">23</A> Somekh L. Shanzer A. J. Am. Chem. Soc. 1982, 104: 5836

<A NAME="RE61011SS-24">24</A> Charvillon FB. Amouroux R. Tetrahedron Lett. 1996, 37: 5103

<A NAME="RE61011SS-25">25</A> Gani D. Hitchcock PB. Young DW. J. Chem. Soc., Perkin Trans. 1 1985, 1363

<A NAME="RE61011SS-26">26</A> Fokina NA. Kornilov AM. Kulik IB. Kukhar VP. Synthesis 2002, 2589

<A NAME="RE61011SS-27">27</A> Davis FA. Reddy RR. Tetrahedron: Asymmetry 1994, 5: 955

<A NAME="RE61011SS-28">28</A> Andrews PC. Bhaskar V. Bromfield KM. Dodd AM. Duggan PJ. Duggan SAM. McCarthy TD. Synlett 2004, 791

<A NAME="RE61011SS-29">29</A> Lee JH. Kim DY. Synthesis 2010, 1860

<A NAME="RE61011SS-30">30</A> Edmonds MK. Graichen FHM. Gardiner J. Abell AD. Org. Lett. 2008, 10: 885

<A NAME="RE61011SS-31A">31a</A> Kieltsch I. Eisenberger P. Togni A. Angew. Chem. Int. Ed. 2007, 46: 754

<A NAME="RE61011SS-31B">31b</A> Kieltsch I. Eisenberger P. Stanek K. Togni A. Chimia 2008, 62: 260

<A NAME="RE61011SS-31C">31c</A> Niedermann K. Welch JM. Koller R. Cvengroš J. Santschi N. Battaglia P. Togni A. Tetrahedron 2010, 66: 5753

<A NAME="RE61011SS-31D">31d</A> Armanino N. Koller R. Togni A. Organometallics 2010, 29: 1771

<A NAME="RE61011SS-31E">31e</A> Wiehn MS. Vinogradova EV. Togni A. J. Fluorine Chem. 2010, 131: 951

<A NAME="RE61011SS-31F">31f</A> Koller R. Togni A. Chim. Oggi/Chem. Today 2010, 28: 33

For another and more direct approach, see:

<A NAME="RE61011SS-31G">31g</A> Soloshonok VA. Kukhar VP. Pustovit Y. Nazaretyan VA. Synlett 1992, 657

<A NAME="RE61011SS-32">32</A> Capone S. Kieltsch I. Flögel O. Lelais G. Togni A. Seebach D. Helv. Chim. Acta 2008, 91: 2035

<A NAME="RE61011SS-33A">33a</A> Drexler H.-J. You J. Zhang S. Fischer C. Baumann W. Spannenberg A. Heller D. Org. Process Res. Dev. 2003, 7: 355

<A NAME="RE61011SS-33B">33b</A> Juaristi E. Gutiérrez-García VM. López-Ruiz H. In Enantioselective Synthesis of β-Amino Acids 2nd ed.: Juaristi EC. Soloshonok VA. Wiley-VCH; Weinheim: 2005. p.159

<A NAME="RE61011SS-34">34</A> Uneyama K. Hao J. Amii H. Tetrahedron Lett. 1998, 39: 4079

<A NAME="RE61011SS-35">35</A> Uneyama K. Ohkura H. Hao J. Amii H. J. Org. Chem. 2001, 66: 1026

<A NAME="RE61011SS-36">36</A> Ohkura H. Handa M. Katagiri T. Uneyama K. J. Org. Chem. 2002, 67: 2692

<A NAME="RE61011SS-37">37</A> Fustero S. Pina B. García de la Torre M. Navarro A. Ramírez de Arellano C. Simón A. Org. Lett. 1999, 1: 977

<A NAME="RE61011SS-38">38</A> Fustero S. Pina B. Salavert E. Navarro A. Ramírez de Arellano C. Simón Fuentes A. J. Org. Chem. 2002, 67: 4667

<A NAME="RE61011SS-39">39</A> Fustero S. Salavert E. Pina B. Ramírez de Arellano C. Asensio A. Tetrahedron 2001, 57: 6475

<A NAME="RE61011SS-40">40</A> Ishida Y. Iwahashi N. Nishizono N. Saigo K. Tetrahedron Lett. 2009, 50: 1889

<A NAME="RE61011SS-41">41</A> Dai Q. Yang W. Zhang X. Org. Lett. 2005, 7: 5343

<A NAME="RE61011SS-42">42</A> Murahashi S.-I. Zhang D. Chem. Soc. Rev. 2008, 37: 1490

<A NAME="RE61011SS-43A">43a</A> Boyall D. Frantz DE. Carreira EM. Org. Lett. 2002, 4: 2605

<A NAME="RE61011SS-43B">43b</A> Soloshonok VA. Berbasov DO. J. Fluorine Chem. 2004, 125: 1757

<A NAME="RE61011SS-43C">43c</A> Moore JL. Taylor SM. Soloshonok VA. ARKIVOC 2005, (vi): 287

<A NAME="RE61011SS-43D">43d</A> Soloshonok VA. Cai C. Yamada T. Ueki H. Ohfune Y. Hruby VJ. J. Am. Chem. Soc. 2005, 127: 15296

<A NAME="RE61011SS-44">44</A> Braunshtein AE. Kritsman MG. Biokhimiya 1937, 2: 859 ; Chem. Abstr. 1938, 32, 25489

<A NAME="RE61011SS-45A">45a</A> Martell AE. Acc. Chem. Res. 1989, 22: 115

<A NAME="RE61011SS-45B">45b</A> Tanner ME. Acc. Chem. Res. 2002, 35: 237

<A NAME="RE61011SS-45C">45c</A> Wachtershauser G. Microbiol. Rev. 1988, 52: 452

<A NAME="RE61011SS-45D">45d</A> Toney MD. Kirsch JF. Biochemistry 1993, 32: 1471

<A NAME="RE61011SS-45E">45e</A> Longenecker JB. Snell EE. J. Am. Chem. Soc. 1957, 79: 142

<A NAME="RE61011SS-46">46</A> Lehninger AL. Nelson DI. Cox MM. Principles of Biochemistry 2nd ed.: Worth Publishers; New York: 1993.

<A NAME="RE61011SS-47">47</A> Casella L. Gullotti M. J. Am. Chem. Soc. 1983, 105: 803

<A NAME="RE61011SS-48A">48a</A> Layer RW. Chem. Rev. 1963, 63: 489

<A NAME="RE61011SS-48B">48b</A> Smith PAS. Van Dang C. J. Org. Chem. 1976, 41: 2013

<A NAME="RE61011SS-49A">49a</A> Liu L. Zhou W. Chruma J. Breslow R. J. Am. Chem. Soc. 2004, 126: 8136

<A NAME="RE61011SS-49B">49b</A> Liu L. Breslow R. J. Am. Chem. Soc. 2003, 125: 12110

<A NAME="RE61011SS-49C">49c</A> Liu L. Rozenman M. Breslow R. J. Am. Chem. Soc. 2002, 124: 12660

<A NAME="RE61011SS-49D">49d</A> Liu L. Breslow R. J. Am. Chem. Soc. 2002, 124: 4978

<A NAME="RE61011SS-50A">50a</A> Soloshonok VA. Ono T. J. Fluorine Chem. 2008, 129: 785

<A NAME="RE61011SS-50B">50b</A> Soloshonok VA. Catt HT. Ono T. J. Fluorine Chem. 2009, 130: 512

<A NAME="RE61011SS-50C">50c</A> Soloshonok VA. Catt HT. Ono T. J. Fluorine Chem. 2010, 131: 261

<A NAME="RE61011SS-50D">50d</A> Han J. Sorochinsky AE. Ono T. Soloshonok VA. Curr. Org. Synth. 2011, 8: 281

<A NAME="RE61011SS-51">51</A> Corey EJ. Achiwa K. J. Am. Chem. Soc. 1969, 91: 1429

<A NAME="RE61011SS-52A">52a</A> Calo V. Lopez L. Todesco PE. J. Chem. Soc., Perkin Trans. 1 1972, 1652

<A NAME="RE61011SS-52B">52b</A> Ohta S. Okamoto M. Synthesis 1982, 756

<A NAME="RE61011SS-52C">52c</A> Buckley TF. Rapoport H. J. Am. Chem. Soc. 1982, 104: 4446

<A NAME="RE61011SS-52D">52d</A> Babler JH. Invergo BJ. J. Org. Chem. 1981, 46: 1937

<A NAME="RE61011SS-53">53</A> Cainelli G. Giacomini D. Trere A. Boyl PP. J. Org. Chem. 1996, 61: 5134

<A NAME="RE61011SS-54A">54a</A> Ando M. Kuzuhara H. Bull. Chem. Soc. Jpn. 1990, 63: 1925

<A NAME="RE61011SS-54B">54b</A> Zimmerman S. Breslow R. J. Am. Chem. Soc. 1984, 106: 1490

<A NAME="RE61011SS-55A">55a</A> Willems JGH. de Vries JG. Nolte RJM. Zwanenburg B. Tetrahedron Lett. 1995, 36: 3917

<A NAME="RE61011SS-55B">55b</A> Hjelmencrantz A. Berg U. J. Org. Chem. 2002, 67: 3585

<A NAME="RE61011SS-55C">55c</A> Wu Y. Ahlberg P. J. Org. Chem. 1992, 57: 6324

<A NAME="RE61011SS-56A">56a</A> Soloshonok VA. Gerus II. Yagupolskii YL. Zh. Org. Khim. 1986, 22: 1335 ; Chem. Abstr. 1987, 106, 19861u

<A NAME="RE61011SS-56B">56b</A> Soloshonok VA. Gerus II. Yagupolskii YL. Kukhar VP. Zh. Org. Khim. 1987, 23: 2308 ; Chem. Abstr. 1988, 109, 6076v

<A NAME="RE61011SS-56C">56c</A> Soloshonok VA. Yagupolskii YL. Kukhar VP. Zh. Org. Khim. 1988, 24: 1638 ; Chem. Abstr. 1989, 110, 154827b

<A NAME="RE61011SS-57">57</A> Ono T. Kukhar VP. Soloshonok VA. J. Org. Chem. 1996, 61: 6563

<A NAME="RE61011SS-58A">58a</A> Kobzev SV. Soloshonok VA. Galushko SV. Yagupolskii YL. Kukhar VP. Zh. Obshch. Khim. 1989, 59: 909 ; Chem. Abstr. 1990, 112, 217474y

<A NAME="RE61011SS-58B">58b</A> Soloshonok VA. Kacharov AD. Hayashi T. Tetrahedron 1996, 52: 245

<A NAME="RE61011SS-59">59</A> Soloshonok VA. Gerus II. Yagupolskii YL. Kukhar VP. Zh. Org. Khim. 1988, 24: 993 ; Chem. Abstr. 1989, 110, 134824v

<A NAME="RE61011SS-60">60</A> Kukhar VP. Sorochinsky AE. Soloshonok VA. Future Med. Chem. 2009, 1: 793

<A NAME="RE61011SS-61A">61a</A> Bravo P. Farina A. Frigerio M. Valdo Meille S. Viani F. Soloshonok VA. Tetrahedron: Asymmetry 1994, 5: 987

<A NAME="RE61011SS-61B">61b</A> Soloshonok VA. Avilov DV. Kukhar VP. Tetrahedron 1996, 52: 12433

<A NAME="RE61011SS-62A">62a</A> Bravo P. Capelli S. Guidetti M. Meille SV. Viani F. Zanda M. Markovsky AL. Sorochinsky AE. Soloshonok VA. Tetrahedron 1999, 55: 3025

<A NAME="RE61011SS-62B">62b</A> Soloshonok VA. Avilov DV. Kukhar VP. Tetrahedron: Asymmetry 1996, 7: 1547

<A NAME="RE61011SS-63A">63a</A> Soloshonok VA. Hayashi T. Ishikawa K. Nagashima N. Tetrahedron Lett. 1994, 35: 1055

<A NAME="RE61011SS-63B">63b</A> Ohkura H. Berbasov DO. Soloshonok VA. Tetrahedron 2003, 59: 1647

<A NAME="RE61011SS-63C">63c</A> Soloshonok VA. Avilov DV. Kukhar VP. Tararov VI. Saveleva TF. Churkina TD. Ikonnikov NS. Kochetkov KA. Orlova SA. Pysarevsky AP. Struchkov YT. Raevsky NI. Belokon YN. Tetrahedron: Asymmetry 1995, 6: 1741

<A NAME="RE61011SS-64A">64a</A> Soloshonok VA. Hayashi T. Tetrahedron Lett. 1994, 35: 2713

<A NAME="RE61011SS-64B">64b</A> Soloshonok VA. Hayashi T. Tetrahedron: Asymmetry 1994, 5: 1091

<A NAME="RE61011SS-65A">65a</A> Soloshonok VA. Ono T. Synlett 1996, 919

<A NAME="RE61011SS-65B">65b</A> Soloshonok VA. Ono T. Tetrahedron 1996, 52: 14701

<A NAME="RE61011SS-65C">65c</A> Yasumoto M. Ueki H. Soloshonok VA. J. Fluorine Chem. 2007, 128: 736

<A NAME="RE61011SS-66A">66a</A> Khotkevich AB. Soloshonok VA. Yagupolskii YL. Zh. Obshch. Khim. 1990, 60: 1005 ; Chem. Abstr. 1990, 113, 171274y

<A NAME="RE61011SS-66B">66b</A> Nagy P. Ueki H. Berbasov DO. Soloshonok VA. J. Fluorine Chem. 2008, 129: 409

<A NAME="RE61011SS-67">67</A> Limbach HH. Maennle F. Detering C. Denisov GS. Chem. Phys. 2005, 319: 69

<A NAME="RE61011SS-68A">68a</A> Soloshonok VA. Kirilenko AG. Kukhar VP. Resnati GA. Tetrahedron Lett. 1994, 35: 3119

<A NAME="RE61011SS-68B">68b</A> Soloshonok VA. Ohkura H. Yasumoto M. Mendeleev Commun. 2006, 165

<A NAME="RE61011SS-69A">69a</A> Ohkura H. Berbasov DO. Soloshonok VA. Tetrahedron Lett. 2003, 44: 2417

<A NAME="RE61011SS-69B">69b</A> Soloshonok VA. Ohkura H. Yasumoto M. J. Fluorine Chem. 2006, 127: 708

<A NAME="RE61011SS-70">70</A> Soloshonok VA. Kukhar VP. Tetrahedron 1997, 53: 8307

<A NAME="RE61011SS-71A">71a</A> Soloshonok VA. Yasumoto M. J. Fluorine Chem. 2006, 127: 889

<A NAME="RE61011SS-71B">71b</A> Berbasov DO. Ojemaye ID. Soloshonok VA. J. Fluorine Chem. 2004, 125: 603

<A NAME="RE61011SS-72">72</A> Soloshonok VA. Ohkura H. Uneyama K. Tetrahedron Lett. 2002, 43: 5449

<A NAME="RE61011SS-73">73</A> Kukhar VP. Soloshonok VA. Galushko SV. Rozhenko AB. Dokl. Akad. Nauk SSSR 1990, 310: 886 ; Chem. Abstr. 1990, 113, 78920w

<A NAME="RE61011SS-74A">74a</A> Soloshonok VA. Kirilenko AG. Kukhar VP. Resnati G. Tetrahedron Lett. 1993, 34: 3621

<A NAME="RE61011SS-74B">74b</A> Soloshonok VA. Kukhar VP. Tetrahedron 1996, 52: 6953

<A NAME="RE61011SS-75A">75a</A> Soloshonok VA. Svedas VK. Kukhar VP. Kirilenko AG. Rybakova AV. Solodenko VA. Fokina NA. Kogut OV. Galaev IY. Kozlova EV. Shishkina IP. Galushko SV. Synlett 1993, 339

<A NAME="RE61011SS-75B">75b</A> Soloshonok VA. Kirilenko AG. Fokina NA. Shishkina IP. Galushko SV. Kukhar VP. Svedas VK. Kozlova EV. Tetrahedron: Asymmetry 1994, 5: 1119

<A NAME="RE61011SS-76A">76a</A> Soloshonok VA. Fokina NA. Rybakova AV. Shishkina IP. Galushko SV. Sorochinsky AE. Kukhar VP. Savchenko MV. Svedas VK. Tetrahedron: Asymmetry 1995, 6: 1601

<A NAME="RE61011SS-76B">76b</A> Soloshonok VA. Kirilenko AG. Fokina NA. Galushko SV. Kukhar VP. Svedas VK. Resnati G. Tetrahedron: Asymmetry 1994, 5: 1225

<A NAME="RE61011SS-77">77</A> Soloshonok VA. Soloshonok IV. Kukhar VP. Svedas VK. J. Org. Chem. 1998, 63: 1878

<A NAME="RE61011SS-78">78</A> Soloshonok VA. Ono T. Soloshonok IV. J. Org. Chem. 1997, 62: 7538

<A NAME="RE61011SS-79">79</A> Soloshonok VA. Ohkura H. Yasumoto M. J. Fluorine Chem. 2006, 127: 924

<A NAME="RE61011SS-80">80</A> Soloshonok VA. Ohkura H. Yasumoto M. J. Fluorine Chem. 2006, 127: 930

<A NAME="RE61011SS-81">81</A> Soloshonok VA. Ono T. J. Org. Chem. 1997, 62: 3030

<A NAME="RE61011SS-82A">82a</A> Soloshonok VA. Angew. Chem. Int. Ed. 2006, 45: 766

<A NAME="RE61011SS-82B">82b</A> Soloshonok VA. Berbasov DO. J. Fluorine Chem. 2006, 127: 597

<A NAME="RE61011SS-82C">82c</A> Soloshonok VA. Berbasov DO. Chim. Oggi/Chem. Today 2006, 24: 44

<A NAME="RE61011SS-83A">83a</A> Soloshonok VA. Ueki H. Yasumoto M. Mekala S. Hirschi JS. Singleton DA. J. Am. Chem. Soc. 2007, 129: 12112

<A NAME="RE61011SS-83B">83b</A> Yasumoto M. Ueki H. Ono T. Katagiri T. Soloshonok VA. J. Fluorine Chem. 2010, 131: 535

<A NAME="RE61011SS-83C">83c</A> Ueki H. Yasumoto M. Soloshonok VA. Tetrahedron: Asymmetry 2010, 21: 1396

<A NAME="RE61011SS-83D">83d</A> Han J. Nelson DJ. Sorochinsky AE. Soloshonok VA. Curr. Org. Synth. 2011, 8: 310

<A NAME="RE61011SS-83E">83e</A> Basiuk VA. Gromovoy TY. Chuiko AA. Soloshonok VA. Kukhar VP. Synthesis 1992, 449

<A NAME="RE61011SS-84">84</A> Soloshonok VA. Kirilenko AG. Galushko SV. Kukhar VP. Tetrahedron Lett. 1994, 35: 5063

<A NAME="RE61011SS-85">85</A> Soloshonok VA. Yasumoto M. J. Fluorine Chem. 2007, 128: 170

<A NAME="RE61011SS-86A">86a</A> Michaut V. Metz F. Paris JM. Plaquevent JC. J. Fluorine Chem. 2007, 128: 500

<A NAME="RE61011SS-86B">86b</A> Michaut V. Metz F. Paris JM. Plaquevent JC. J. Fluorine Chem. 2007, 128: 889

<A NAME="RE61011SS-87">87</A> Miller SJ. Guerin DJ. In Enantioselective Synthesis of β-Amino Acids 2nd ed.: Juaristi EC. Soloshonok VA. Wiley-VCH; Weinheim: 2005. p.351

<A NAME="RE61011SS-88">88</A> Volonterio A. Bravo P. Zanda M. Org. Lett. 2000, 13: 1827

<A NAME="RE61011SS-89A">89a</A> Volonterio A. Bravo P. Zanda M. Tetrahedron Lett. 2001, 42: 3141

<A NAME="RE61011SS-89B">89b</A> Volonterio A. Bravo P. Moussier N. Zanda M. Tetrahedron Lett. 2000, 41: 6517

<A NAME="RE61011SS-89C">89c</A> Bravo P. Capelli S. Meille SV. Viani F. Zanda M. Kukhar VP. Soloshonok VA. Tetrahedron: Asymmetry 1994, 5: 2009

<A NAME="RE61011SS-90">90</A> Volonterio A. Bellosta S. Bravo P. Canavesi M. Corradi E. Meille SV. Monetti M. Moussier N. Zanda M. Eur. J. Org. Chem. 2002, 428

<A NAME="RE61011SS-91">91</A> Molteni M. Volonterio A. Fossati G. Lazzari P. Zanda M. Tetrahedron Lett. 2007, 48: 589

<A NAME="RE61011SS-92">92</A> Formicola L. Marechal X. Basse N. Bouvier-Durand M. Bonnet-Delpon D. Milcent T. Reboud-Ravaux M. Ongeri S. Bioorg. Med. Chem. Lett. 2009, 19: 83

<A NAME="RE61011SS-93">93</A> Weiss M. Gröger H. Synlett 2009, 1251

<A NAME="RE61011SS-94">94</A> Colantoni D. Fioravanti S. Pellacani L. Tardella PA. Org. Lett. 2004, 6: 197

<A NAME="RE61011SS-95">95</A> Sani M. Bruche L. Chiva G. Fustero S. Piera J. Volonterio A. Zanda M. Angew. Chem. Int. Ed. 2003, 42: 2060

<A NAME="RE61011SS-96A">96a</A> Volonterio A. Chiva G. Fustero S. Piera J. Sanchez RM. Sani M. Zanda M. Tetrahedron Lett. 2003, 44: 7019

<A NAME="RE61011SS-96B">96b</A> Bravo P. Farina A. Kukhar VP. Markovsky AL. Meille SV. Soloshonok VA. Sorochinsky AE. Viani F. Zanda M. Zappala C. J. Org. Chem. 1997, 62: 3424

<A NAME="RE61011SS-97">97</A> Fustero S. Garcia SA. Chiva G. Sanz-Cervera JF. Del Pozo C. Acena JL. J. Org. Chem. 2006, 71: 3299

<A NAME="RE61011SS-98">98</A> Fustero S. Chiva G. Piera J. Sanz-Cervera JF. Volonterio A. Zanda M. Ramirez de Arellano C. J. Org. Chem. 2009, 74: 3122

<A NAME="RE61011SS-99">99</A> Fustero S. Chiva G. Piera J. Volonterio A. Zanda M. Gonzalez J. Ramallal AM. Chem. Eur. J. 2007, 13: 8530

<A NAME="RE61011SS-100">100</A> Ocampoa R. Dolbier WR. Tetrahedron 2004, 60: 9325

<A NAME="RE61011SS-101">101</A> Ishii A. Miyamoto F. Higashiyama K. Mikami K. Tetrahedron 1998, 39: 1199

<A NAME="RE61011SS-102">102</A> Dos Santos M. Crousse B. Bonnet-Delpon D. Synlett 2008, 399

<A NAME="RE61011SS-103">103</A> Ishii A. Higashiyama K. Mikami K. Synlett 1997, 1381

<A NAME="RE61011SS-104">104</A> Huguenot F. Brigaud T. J. Org. Chem. 2006, 71: 2159

<A NAME="RE61011SS-105">105</A> Truong VL. Ménard MS. Dion I. Org. Lett. 2007, 9: 683

<A NAME="RE61011SS-106">106</A> Mimura H. Kawada K. Yamashita T. Sakamoto T. Kikugawa Y. J. Fluorine Chem. 2010, 131: 477

<A NAME="RE61011SS-107">107</A> Tarui A. Sato K. Omote M. Kumadaki I. Andoa A. Adv. Synth. Catal. 2010, 352: 2733

<A NAME="RE61011SS-108A">108a</A> Taguchi T. Kitagawa O. Suda Y. Ohkawa S. Hashimoto A. Itaka Y. Kobayashi Y. Tetrahedron Lett. 1988, 29: 5291

<A NAME="RE61011SS-108B">108b</A> Angelastro MR. Bey P. Hehdi S. Peet NP. Bioorg. Med. Chem. Lett. 1992, 2: 1235

<A NAME="RE61011SS-108C">108c</A> Van Brabandt W. De Kimpe N. Synlett 2006, 2039

<A NAME="RE61011SS-108D">108d</A> Boyer N. Gloanec P. De Nanteuil G. Jubault P. Quirion J.-C. Tetrahedron 2007, 63: 12352

<A NAME="RE61011SS-108E">108e</A> Boyer N. Gloanec P. De Nanteuil G. Jubault P. Quirion J.-C. Eur. J. Org. Chem. 2008, 4277

<A NAME="RE61011SS-109">109</A> Sato K. Tarui A. Matsuda S. Omote M. Ando A. Kumadaki I. Tetrahedron Lett. 2005, 46: 7679

<A NAME="RE61011SS-110">110</A> Katritzky AR. Nichols DA. Qi M. Tetrahedron Lett. 1998, 39: 7063

<A NAME="RE61011SS-111">111</A> Vidal A. Nefzi A. Houghten RA. J. Org. Chem. 2001, 66: 8268

<A NAME="RE61011SS-112A">112a</A> Baldwin JE. Lynch GP. Schofield CJ. Tetrahedron 1992, 48: 9085

<A NAME="RE61011SS-112B">112b</A> Tarui A. Kondo K. Taira H. Sato K. Omote M. Kumadaki I. Ando A. Heterocycles 2007, 73: 203

<A NAME="RE61011SS-113">113</A> Marcotte S. Pannecoucke X. Feasson C. Quirion J.-C. J. Org. Chem. 1999, 64: 8461

<A NAME="RE61011SS-114">114</A> Barton D. Easdon J. J. Fluorine Chem. 1988, 38: 125

<A NAME="RE61011SS-115">115</A> Otaka A. Watanabe J. Yukimasa A. Sasaki Y. Watanabe H. Kinoshita T. Oishi S. Tamamura H. Fujii N. J. Org. Chem. 2004, 69: 1634

<A NAME="RE61011SS-116A">116a</A> Zhou P. Chen B. Davis F. Tetrahedron 2004, 60: 8003

<A NAME="RE61011SS-116B">116b</A> Morton D. Stockman R. Tetrahedron 2006, 62: 8869

<A NAME="RE61011SS-117A">117a</A> Soloshonok VA. Ohkura H. Sorochinsky A. Voloshin N. Markovsky A. Belik M. Yamazaki T. Tetrahedron Lett. 2002, 43: 5445

<A NAME="RE61011SS-117B">117b</A> Sorochinsky A. Voloshin N. Markovsky A. Belik M. Yasuda N. Uekusa H. Ono T. Berbasov DO. Soloshonok VA. J. Org. Chem. 2003, 68: 7448

<A NAME="RE61011SS-118">118</A> Robak M.-AT. Herbage MA. Ellman JA. Chem. Rev. 2010, 110: 3600

<A NAME="RE61011SS-119A">119a</A> Staas DD. Savage KL. Homnick CF. Tsou NN. Ball RG. J. Org. Chem. 2002, 67: 8276

<A NAME="RE61011SS-119B">119b</A> Christianson CV. Montavon TJ. Festin GM. Cooke HA. Shen B. Bruner SD. J. Am. Chem. Soc. 2007, 129: 15744

<A NAME="RE61011SS-120">120</A> Sekiguchi T. Sato K. Ishihara T. Konno T. Yamanaka H. Chem. Lett. 2004, 33: 666

<A NAME="RE61011SS-121">121</A> Tarui A. Ozaki D. Nakajima N. Yokota Y. Sokeirik YS. Sato K. Omote M. Kumadaki I. Ando A. Tetrahedron Lett. 2008, 49: 3839

<A NAME="RE61011SS-122">122</A> Shimada T. Yoshioka M. Konno T. Ishihara T. Chem. Commun. 2006, 3628

<A NAME="RE61011SS-123">123</A> Tarui A. Kawashima N. Sato K. Omote M. Miwa Y. Minami H. Ando A. Tetrahedron Lett. 2010, 51: 2000

<A NAME="RE61011SS-124">124</A> Tarui A. Kawashima N. Sato K. Omote M. Ando A. Tetrahedron Lett. 2010, 51: 4246

<A NAME="RE61011SS-125A">125a</A> Bhadury PS. Song B.-A. Curr. Org. Chem. 2010, 14: 1989

<A NAME="RE61011SS-125B">125b</A> Verkade JMM. van Hemert LJC. Quaedflieg PJLM. Rutjes FPJT. Chem. Soc. Rev. 2008, 37: 29

<A NAME="RE61011SS-125C">125c</A> Ting A. Schaus SE. Eur. J. Org. Chem. 2007, 5797

<A NAME="RE61011SS-126">126</A> Lazzaro F. Crucianelli M. De Angelis F. Frigerio M. Malpezzi L. Volonterio A. Zanda M. Tetrahedron: Asymmetry 2004, 15: 889

<A NAME="RE61011SS-127">127</A> Fustero S. Jiménez D. Sanz-Cervera JF. Sánchez-Roselló M. Esteban E. Simón-Fuentes A. Org. Lett. 2005, 7: 3433

<A NAME="RE61011SS-128">128</A> Fustero S. Mojarrad F. Pérez Carrión MD. Sanz-Cervera JF. Aceña JL. Eur. J. Org. Chem. 2009, 5208

<A NAME="RE61011SS-129A">129a</A> Soloshonok VA. Avilov DV. Kukhar VP. Van Meervelt L. Mischenko N. Tetrahedron Lett. 1997, 38: 4671

<A NAME="RE61011SS-129B">129b</A> Soloshonok VA. Kukhar VP. Galushko SV. Svistunova NY. Avilov DV. Kuzmina NA. Raevski NI. Struchkov YT. Pisarevsky AP. Belokon YN. J. Chem. Soc., Perkin Trans. 1 1993, 3143

<A NAME="RE61011SS-130">130</A> Chung WJ. Omote M. Welch JT. J. Org. Chem. 2005, 70: 7784

<A NAME="RE61011SS-131">131</A> Kashikura W. Mori K. Akiyama T. Org. Lett. 2011, 13: 1860

<A NAME="RE61011SS-132">132</A> Pan Y. Zhao Y. Ma T. Yang Y. Liu H. Jiang Z. Tan C.-H. Chem. Eur. J. 2010, 16: 779

<A NAME="RE61011SS-133">133</A> Zhang F. Liu Z.-J. Liu J.-T. Org. Biomol. Chem. 2011, 9: 3625

<A NAME="RE61011SS-134">134</A> Crousse B. Narizuka S. Bonnet-Delpon D. Bégué J.-P. Synlett 2001, 679

<A NAME="RE61011SS-135">135</A> Akiyama T. Ogi S. Fuchibe K. Tetrahedron Lett. 2003, 44: 4011

<A NAME="RE61011SS-136">136</A> Spanedda MV. Narizuka S. Crousse B. Bonnet-Delpon D. Bégué J.-P. Collect. Czech. Chem. Commun. 2002, 67: 1359

<A NAME="RE61011SS-137">137</A> Prati F. Moretti I. Forni A. Torre G. Rozhkov VV. Makarov KN. Chervin II. Kostyanovsky RG. J. Fluorine Chem. 1998, 89: 177

<A NAME="RE61011SS-138">138</A> Davoli P. Forni A. Franciosi C. Moretti I. Prati F. Tetrahedron: Asymmetry 1999, 10: 2361

<A NAME="RE61011SS-139">139</A> Rinaudo G. Narizuka S. Askari N. Crousse B. Bonnet-Delpon D. Tetrahedron Lett. 2006, 47: 2065

<A NAME="RE61011SS-140A">140a</A> Abouabdellah A. Bégué J.-P. Bonnet-Delpon D. Synlett 1996, 399

<A NAME="RE61011SS-140B">140b</A> Abouabdellah A. Bégué J.-P. Bonnet-Delpon D. Thanh Nga TT. J. Org. Chem. 1997, 62: 8826

<A NAME="RE61011SS-140C">140c</A> Ojima I. Slater JC. Chirality 1997, 9: 487

<A NAME="RE61011SS-140D">140d</A> Lin S. Geng XD. Qu CX. Tynebor R. G allagher DJ. Pollina E. Rutter J. Ojima I. Chirality 2000, 12: 431

<A NAME="RE61011SS-141">141</A> Abouabdellah A. Bégué J.-P. Bonnet-Delpon D. Kornilov A. Rodrigues I. Thanh Nga TT. In Asymmetric Fluoroorganic Chemistry: Synthesis, Application and Future Directions ACS Symposium Series 746: Ramachandran PV. American Chemical Society; Washington: 2000. p.84

<A NAME="RE61011SS-142">142</A> Jakowiecki J. Loska R. Makosza M. J. Org. Chem. 2008, 73: 5436

<A NAME="RE61011SS-143">143</A> For a review on addition reactions of allylic metal reagents, see: Gung BW. Org. React. 2004, 65: 1

<A NAME="RE61011SS-144">144</A> Sergeeva NN. Golubev AS. Hennig L. Burger K. Synthesis 2002, 2579

<A NAME="RE61011SS-145">145</A> Legros J. Meyer F. Coliboeuf M. Crousse B. Bonnet-Delpon D. Bégué J.-P. J. Org. Chem. 2003, 68: 6444

<A NAME="RE61011SS-146">146</A> Kuduk SD. Marco CND. Pitzenberger SM. Tsou N. Tetrahedron Lett. 2006, 47: 2377

<A NAME="RE61011SS-147">147</A> Magueur G. Legros J. Meyer F. Ourévitch M. Crousse B. Bonnet-Delpon D. Eur. J. Org. Chem. 2005, 1258

<A NAME="RE61011SS-148">148</A> For a review on the SAMP/RAMP hydrazone method, see: Job A. Janeck CF. Bettray W. Peters R. Enders D. Tetrahedron 2002, 58: 2253

<A NAME="RE61011SS-149">149</A> Funabiki K. Nagamori M. Matsui M. Enders D. Synthesis 2002, 2585

<A NAME="RE61011SS-150">150</A> Funabiki K. Nagamori M. Matsui M. J. Fluorine Chem. 2005, 126: 705

<A NAME="RE61011SS-151">151</A> Funabiki K. Nagamori M. Matsui M. J. Fluorine Chem. 2004, 125: 1347

<A NAME="RE61011SS-152">152</A> Fustero S. del Pozo C. Catalán S. Alemán J. Parra A. Marcos V. García Ruano JL. Org. Lett. 2009, 11: 641

<A NAME="RE61011SS-153">153</A> Grubbs RH. Handbook of Metathesis Wiley-VCH; Weinheim: 2003.

<A NAME="RE61011SS-154A">154a</A> Sundararaju B. Sridhar T. Achard M. Sharma GVM. Bruneau C. Eur. J. Org. Chem. 2010, 6092

<A NAME="RE61011SS-154B">154b</A> Gardiner J. Aitken SG. McNabb SB. Zaman S. Abell AD. J. Organomet. Chem. 2006, 691: 5487

<A NAME="RE61011SS-154C">154c</A> Lesma G. Danieli B. Sacchetti A. Silvani A. J. Org. Chem. 2006, 71: 3317

<A NAME="RE61011SS-154D">154d</A> Yamanaka T. Ohkubo M. Kato M. Kawamura Y. Nishi A. Synlett 2005, 631

<A NAME="RE61011SS-154E">154e</A> Gardiner J. Anderson KH. Downard A. Abell AD. J. Org. Chem. 2004, 69: 3375

<A NAME="RE61011SS-154F">154f</A> Chippindale AM. Davies SG. Iwamoto K. Parkin RM. Smethurst CAP. Smith AD. Rodriguez-Solla H. Tetrahedron 2003, 59: 3253

<A NAME="RE61011SS-154G">154g</A> Perlmutter P. Rose M. Vounatsos F. Eur. J. Org. Chem. 2003, 756

<A NAME="RE61011SS-155">155</A> Elaridi J. Jackson WR. Robinson AJ. Tetrahedron: Asymmetry 2005, 16: 2025

<A NAME="RE61011SS-156A">156a</A> Mittendorf J. Kunisch F. Matzke M. Militzer H.-C. Schmidt A. Schönfeld W. Bioorg. Med. Chem. Lett. 2003, 13: 433

<A NAME="RE61011SS-156B">156b</A> Vera-Ayoso Y. Borrachero P. Cabrera-Escribano F. Diánez MJ. Estrada MD. Gómez-Guillén M. López-Castro A. Pérez-Garrido S. Tetrahedron: Asymmetry 2001, 12: 2031

<A NAME="RE61011SS-157">157</A> Fustero S. Bartolomé A. Sanz-Cervera JF. Sánchez-Roselló M. García-Soler J. Ramírez de Arellano C. Simón-Fuentes A. Org. Lett. 2003, 5: 2523

<A NAME="RE61011SS-158A">158a</A> Fustero S. Sánchez-Roselló M. Sanz-Cervera JF. Aceña JL. del Pozo C. Fernández B. Bartolomé A. Asensio A. Org. Lett. 2006, 8: 4633

<A NAME="RE61011SS-158B">158b</A> Fustero S. Sánchez-Roselló M. Aceña JL. Fernández B. Asensio A. Sanz-Cervera JF. del Pozo C. J. Org. Chem. 2009, 74: 3414

<A NAME="RE61011SS-159A">159a</A> Tamura K. Mizukami H. Maeda K. Watanabe H. Uneyama K. J. Org. Chem. 1993, 58: 32

<A NAME="RE61011SS-159B">159b</A> Uneyama K. Amii H. Katagiri T. Kobayashi T. Hosokawa T. J. Fluorine Chem. 2005, 126: 165

<A NAME="RE61011SS-160A">160a</A> Jiang ZX. Qin YY. Qing FL. J. Org. Chem. 2003, 68: 7544

<A NAME="RE61011SS-160B">160b</A> Jiang Z.-X. Qing F.-L. J. Org. Chem. 2004, 69: 5486

<A NAME="RE61011SS-161">161</A> Avenoza A. Busto JH. Jiménez-Osés G. Peregrina JM. J. Org. Chem. 2005, 70: 5721

<A NAME="RE61011SS-162A">162a</A> Katagiri T. Ihara H. Takahashi M. Kashino S. Furuhashi K. Uneyama K. Tetrahedron: Asymmetry 1997, 8: 2933

<A NAME="RE61011SS-162B">162b</A> Yamauchi Y. Kawate T. Katagiri T. Uneyama K. Tetrahedron Lett. 2003, 44: 6319

<A NAME="RE61011SS-163">163</A> Yamauchi Y. Kawate T. Katagiri T. Uneyama K. Tetrahedron 2003, 59: 9839

<A NAME="RE61011SS-164">164</A> Van Hende E. Verniest G. Deroose F. Thuring J.-W. Macdonald G. De Kimpe N. J. Org. Chem. 2009, 74: 2250

<A NAME="RE61011SS-165">165</A> Iseki K. Kuroki Y. Asada D. Takahoshi M. Kishimoto S. Kobayashi Y. Tetrahedron 1997, 53: 10271

<A NAME="RE61011SS-166A">166a</A> Fokina N. Kornilov A. Kukhar V. J. Fluorine Chem. 2001, 111: 69

<A NAME="RE61011SS-166B">166b</A> Ema T. Kadoya T. Akihara K. Sakai T. J. Mol. Catal. B: Enzym. 2010, 66: 198

<A NAME="RE61011SS-167">167</A> Sergeeva NN. Golubev AS. Hennig L. Findeisen M. Paetzold E. Oehme G. Burger K. J. Fluorine Chem. 2001, 111: 41

<A NAME="RE61011SS-168">168</A> Uneyama K. Mizutani G. Maeda K. Kato T. J. Org. Chem. 1999, 64: 671

<A NAME="RE61011SS-169">169</A> Petrik V. Röschenthaler G.-V. Cahard D. Tetrahedron 2011, 67: 3254