[2.2]Paracyclophane
Derivatives: Synthesis and Application in Catalysis

Jan Paradies

doi:10.1055/s-0031-1289296

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2011(23): 3749-3766
DOI: 10.1055/s-0031-1289296

REVIEW

[2.2]Paracyclophane Derivatives: Synthesis and Application in Catalysis

Jan Paradies*
Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)60845637; e-Mail: jan.paradies@kit.edu;

Weitere Informationen

Publikationsverlauf

Received 1 September 2011
Publikationsdatum:
19. Oktober 2011 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Advances in the field of [2.2]paracyclophane chemistry are reviewed including syntheses, resolution of enantiomers and application in organic synthesis. Transition-metal catalyzed as well as organocatalytic transformations are presented focusing on the development of [2.2]paracyclophane derived ligands and catalysts.

1 Introduction

2 [2.2]Paracyclophane Syntheses

3 Ligand Design on the Basis of [2.2]Paracyclophane

4 Application in Asymmetric Catalysis

4.1 Addition of Organozinc Reagents to Carbonyl Compounds

4.2 Application of [2.2]Paracyclophane-Derived Phosphines

4.2.1 Hydrogenation Reactions

4.2.2 Transition-Metal-Catalyzed C-C and C-X Bond Formation Employing Planar-Chiral Phosphines

4.2.3 Planar-Chiral Carbenes

4.2.4 [2.2]Paracyclophanes in Organocatalysis

5 Summary

Key words

[2.2]paracyclophane - catalyst - asymmetric synthesis - phosphine - carbine - hydrogen bond - hydrogenation - cross-coupling

References

1a Gleiter R. Hopf H. Modern Cyclophane Chemistry Wiley-VCH; Weinheim: 2004.

Google Scholar
1b Vögtle F. Cyclophane Chemistry Wiley; New York: 1993.

Google Scholar
2 Hopf H. Angew. Chem. Int. Ed. 2008, 47: 9808 ; Angew. Chem. 2008, 120, 9954

Google Scholar
3 Pye PJ. Rossen K. Reamer RA. Tsou NN. Volante RP. Reider PJ. J. Am. Chem. Soc. 1997, 119: 6207

Google Scholar
4 Rozenberg V. Sergeeva E. Hopf H. In Modern Cyclophane Chemistry Gleiter R. Hopf H. Wiley-VCH; Weinheim: 2004. p.435-462

Google Scholar
5 Gibson SE. Knight JD. Org. Biomol. Chem. 2003, 1: 1256

Google Scholar
6a Hopf H. Org. Synth. 1981, 60: 41

Google Scholar
6b Winberg HE. Fawcett FS. Org. Synth., Coll. Vol. V Wiley and Sons; New York: 1973. p.883

Google Scholar
6c Winberg HE. Fawcett FS. Mochel WE. Theobald CW. J. Am. Chem. Soc. 1960, 82: 1428

Google Scholar
7 Longone DT. Reetz MT. Chem. Commun. 1967, 46

Google Scholar
8 Chow H.-F. Low K.-H. Wong KY. Synlett 2005, 2130

Google Scholar
9 Dolbier WR. Xie P. Zhang L. Xu W. Chang Y. Abboud KA. J. Org. Chem. 2008, 73: 2469

Google Scholar
10 Zhang L. Ogawa K. Ghiviriga I. Dolbier WR.
J. Org. Chem. 2009, 74: 6831

Google Scholar
11 Friedmann CJ. Ay S. Bräse S. J. Org. Chem. 2010, 75: 4612

Google Scholar
12 Rowlands GJ. Seacome RJ. Beilstein J. Org. Chem. 2009, No. 5

Google Scholar
13a Rowlands GJ. Org. Biomol. Chem. 2008, 6: 1527

Google Scholar
13b Hitchcock PB. Rowlands GJ. Seacome RJ. Org. Biomol. Chem. 2005, 3: 3873

Google Scholar
14 Reich HJ. Yelm KE. J. Org. Chem. 1991, 56: 5672

Google Scholar
15a Quesnelle C. Iihama T. Aubert T. Perrier H. Snieckus V. Tetrahedron Lett. 1992, 33: 2625

Google Scholar
15b Snieckus V. Chem. Rev. 1990, 90: 879

Google Scholar
16a Knochel P. Melzig L. Rauhut CB. Naredi-Rainer N. Chem. Eur. J. 2011, 17: 5361

Google Scholar
16b Knochel P. Melzig L. Rauhut CB. Synthesis 2009, 1041

Google Scholar
16c Knochel P. Melzig L. Rauhut CB. Chem. Commun. 2009, 3536

Google Scholar
16d Knochel P. Rauhut CB. Melzig L. Org. Lett. 2008, 10: 3891

Google Scholar
16e Kopp F. Sklute G. Polborn K. Marek I. Knochel P. Org. Lett. 2005, 7: 3789

Google Scholar
17a Parmar R. Coles MP. Hitchcock PB. Rowlands GJ. Synthesis 2010, 4177

Google Scholar
17b Hitchcock PB. Rowlands GJ. Parmar R. Chem. Commun. 2005, 4219

Google Scholar
18 Jiang B. Zhao X.-L. Tetrahedron: Asymmetry 2004, 15: 1141

Google Scholar
19 Zhuravsky R. Starikova Z. Vorontsov E. Rozenberg V. Tetrahedron: Asymmetry 2008, 19: 216

Google Scholar
20 Braddock DC. MacGilp ID. Perry BG. J. Org. Chem. 2002, 67: 8679

Google Scholar
21a Rozenberg V. Zhuravsky R. Sergeeva E. Chirality 2006, 18: 95

Google Scholar
21b Rozenberg VI. Antonov DY. Zhuravsky RP. Vorontsov EV. Starikova ZA. Tetrahedron Lett. 2003, 44: 3801

Google Scholar
22 Kreis M. Nieger M. Bräse S. J. Organomet. Chem. 2006, 691: 2171

Google Scholar
23a Duthaler RO. Hafner A. Chem. Rev. 1992, 92: 807

Google Scholar
23b Soai K. Niwa S. Chem. Rev. 1992, 92: 833

Google Scholar
23c Rossiter BE. Swingle NM. Chem. Rev. 1992, 92: 771

Google Scholar
24a Maruoka K. Pure Appl. Chem. 2002, 74: 123

Google Scholar
24b Maruoka K. Ooi T. Miura T. Angew. Chem. Int. Ed. 1998, 37: 2347 ; Angew. Chem. 1998, 110, 2524

Google Scholar
24c Lewis Acid Reagents: A Practical Approach Yamamoto H. Oxford University Press; New York: 1999.

Google Scholar
25 Sergeeva EV. Rozenberg VI. Antonov DY. Vorontsov EV. Starikova ZA. Fedyanin IV. Hopf H. Chem. Eur. J. 2005, 11: 6944

Google Scholar
26a Atkinson RCJ. Gibson VC. Long NJ. Chem. Soc. Rev. 2004, 33: 313

Google Scholar
26b Colacot TJ. Chem. Rev. 2003, 103: 3101

Google Scholar
27a Togni A. Haltermann RL. Metallocenes Wiley-VCH; Weinheim: 1998.

Google Scholar
27b Togni A. Angew. Chem. Int. Ed. 1996, 35: 1475 ; Angew. Chem. 1996, 108, 1581

Google Scholar
27c Togni A. Ferrocenes: Homogeneous Catalysis/Organic Synthesis/Materials Science Wiley-VCH; Weinheim: 1994.

Google Scholar
28 Rozenberg VI. Danilova TI. Sergeeva EV. Shouklov IA. Starikova ZA. Hopf H. Kuhlein K. Eur. J. Org. Chem. 2003, 432

Google Scholar
29 Enders D. Noll S. Raabe G. Runsink J. Synthesis 2008, 1288

Google Scholar
30 Enders D. Noll S. Bats JW. Synlett 2005, 2679

Google Scholar
31 Enders D. Job A. Janeck CF. Bettray W. Peters R. Tetrahedron 2002, 58: 2253

Google Scholar
32 Bosnich B. Gavrilova AL. Chem. Rev. 2004, 104: 349

Google Scholar
33a Gladiali S. Mroczek A. Erre G. Taras R. Tetrahedron: Asymmetry 2010, 21: 1921

Google Scholar
33b Stoccoro S. Soro B. Minghetti G. Zucca A. Cinellu MA. Manassero M. Gladiali S. Inorg. Chim. Acta 2006, 359: 1879

Google Scholar
33c Chelucci G. Murineddu G. Pinna GA. Tetrahedron: Asymmetry 2004, 15: 1373

Google Scholar
33d von Zelewsky A. Mamula O. Coord. Chem. Rev. 2003, 242: 87

Google Scholar
33e Chelucci G. Gladiali S. Sanna MG. Brunner H. Tetrahedron: Asymmetry 2000, 11: 3419

Google Scholar
33f Bark T. Von Zelewsky A. Chimia 2000, 54: 589

Google Scholar
33g Bolm C. Schlingloff G. Harms K. Chem. Ber. 1992, 125: 1191

Google Scholar
33h Bolm C. Tetrahedron: Asymmetry 1991, 2: 701

Google Scholar
34 Fu GC. Acc. Chem. Res. 2006, 39: 853

Google Scholar
35a Wörsdörfer U. Vögtle F. Glorius F. Pfaltz A. J. Prakt. Chem. 1999, 341: 445

Google Scholar
35b Wörsdörfer U. Vögtle F. Nieger M. Waletzke M. Grimme S. Glorius F. Pfaltz A. Synthesis 1999, 597

Google Scholar
36 Hopf H. Aly AA. Swaminathan VN. Ernst L. Dix I. Jones PG. Eur. J. Org. Chem. 2004, 68

Google Scholar
37 Ricci G. Ruzziconi R. Giorgio E. J. Org. Chem. 2005, 70: 1011

Google Scholar
38 Falk H. Reichroh P. Schlögl K. Tetrahedron 1970, 26: 511

Google Scholar
39 Pu L. Yu HB. Chem. Rev. 2001, 101: 757

Google Scholar
40a Kozlowski MC. Fennie MW. DiMauro EF. O’brien EM. Annamalai V. Tetrahedron 2005, 61: 6249

Google Scholar
40b Dahmen S. Bräse S. Chem. Commun. 2002, 26

Google Scholar
40c Carreira EM. Frantz DE. Fassler R. J. Am. Chem. Soc. 2000, 122: 1806

Google Scholar
40d Ye MC. Logaraj S. Jackman LM. Hillegass K. Hirsh KA. Bollinger AM. Grosz AL. Mani V. Tetrahedron 1994, 50: 6109

Google Scholar
41a Rozenberg V. Danilova T. Sergeeva E. Vorontsov E. Starikova Z. Korlyukov A. Hopf H. Eur. J. Org. Chem. 2002, 468

Google Scholar
41b Hopf H. Barrett DG. Liebigs Ann. 1995, 449

Google Scholar
41c Antonov DY. Belokon YN. Ikonnikov NS. Orlova SA. Pisarevsky AP. Raevski NI. Rozenberg VI. Sergeeva EV. Struchkov YT. Tararov VI. Vorontsov EV. J. Chem. Soc., Perkin Trans. 1 1995, 1873

Google Scholar
41d Rozenberg V. Kharitonov V. Antonov D. Sergeeva E. Aleshkin A. Ikonnikov N. Orlova S. Belokon Y. Angew. Chem. Int. Ed. 1994, 33: 91 ; Angew. Chem. 1994, 106, 106

Google Scholar
42a Dahmen S. Org. Lett. 2004, 6: 2113

Google Scholar
42b Dahmen S. Bräse S. Org. Lett. 2001, 3: 4119

Google Scholar
43 Höfener S. Lauterwasser F. Bräse S. Adv. Synth. Catal. 2004, 346: 755

Google Scholar
44a Kagan HB. Girard C. Angew. Chem. Int. Ed. 1998, 37: 2923 ; Angew. Chem. 1998, 110, 3088

Google Scholar
44b Kitamura M. Okada S. Suga S. Noyori R. J. Am. Chem. Soc. 1989, 111: 4028

Google Scholar
45 Lauterwasser F. Vanderheiden S. Bräse S. Adv. Synth. Catal. 2006, 348: 443

Google Scholar
46a Podlech J. Gehring T. Angew. Chem. Int. Ed. 2005, 44: 5776 ; Angew. Chem. 2005, 117, 5922

Google Scholar
46b Bolm C. Bienewald F. Seger A. Angew. Chem. Int. Ed. 1996, 35: 1657 ; Angew. Chem. 1994, 108, 1767

Google Scholar
46c Soai K. Hori H. Kawahara M. J. Chem. Soc., Chem. Commun. 1992, 106

Google Scholar
46d Soai K. Niwa S. Hori H. J. Chem. Soc., Chem. Commun. 1990, 982

Google Scholar
47 Antonov DY. Rozenberg VI. Danilova TI. Starikova ZA. Hopf H. Eur. J. Org. Chem. 2008, 1038

Google Scholar
48 Rozenberg VI. Antonov DY. Sergeeva EV. Vorontsov EV. Starikova ZA. Fedyanin IV. Schulz C. Hopf H. Eur. J. Org. Chem. 2003, 2056

Google Scholar
49 Bolm C. Whelligan DK. Adv. Synth. Catal. 2006, 348: 2093

Google Scholar
50 Xin DY. Ma YD. He FY. Tetrahedron: Asymmetry 2010, 21: 333

Google Scholar
51 Danilova TI. Rozenberg VI. Sergeeva EV. Starikova ZA. Bräse S. Tetrahedron: Asymmetry 2003, 14: 2013

Google Scholar
52 Belokon Y. Moscalenko M. Ikonnikov N. Yashkina L. Antonov D. Vorontsov E. Rozenberg V. Tetrahedron: Asymmetry 1997, 8: 3245

Google Scholar
53a Garcia H. Baleizao C. Chem. Rev. 2006, 106: 3987

Google Scholar
53b Gilheany DG. McGarrigle EM. Chem. Rev. 2005, 105: 1563

Google Scholar
54 Hosoya N. Hatayama A. Irie R. Sasaki H. Katsuki T. Tetrahedron 1994, 50: 4311

Google Scholar
55 Shi M. Wang CJ. Tetrahedron: Asymmetry 2002, 13: 2161

Google Scholar
56 Sawamura M. Sasaki H. Nakata T. Ito Y. Bull. Chem. Soc. Jpn. 1993, 66: 2725

Google Scholar
57a Danilova TI. Rozenberg VI. Starikova ZA. Bräse S. Tetrahedron: Asymmetry 2004, 15: 223

Google Scholar
57b Danilova TI. Rozenberg VI. Vorontsov EV. Starikova ZA. Hopf H. Tetrahedron: Asymmetry 2003, 14: 1375

Google Scholar
58a Kelly BG. Gilheany DG. Tetrahedron Lett. 2002, 43: 887

Google Scholar
58b Krause N. Hoffmann-Roder A. Synthesis 2001, 171

Google Scholar
59 Knochel P. Perea JJA. Jones P. Tetrahedron 1998, 54: 8275

Google Scholar
60a Sprout CM. Seto CT. J. Org. Chem. 2003, 68: 7788

Google Scholar
60b Nugent WA. Org. Lett. 2002, 4: 2133

Google Scholar
60c Long J. Ding KL. Angew. Chem. Int. Ed. 2001, 40: 544 ; Angew. Chem. 2001, 113, 562

Google Scholar
61a Ay S. Ziegert RE. Zhang H. Nieger M. Rissanen K. Fink K. Kubas A. Gschwind RM. Bräse S. J. Am. Chem. Soc. 2010, 132: 12899

Google Scholar
61b Ay S. Nieger M. Bräse S. Chem. Eur. J. 2008, 14: 11539

Google Scholar
61c Bräse S. Hoefener S. Angew. Chem. Int. Ed. 2005, 44: 7879 ; Angew. Chem. 2005, 117, 8091

Google Scholar
62 Bräse S. Hermanns N. Dahmen S. Bolm C. Angew. Chem. Int. Ed. 2002, 41: 3692 ; Angew. Chem. 2002, 114, 3844

Google Scholar
63 Pietrusiewicz KM. Zablocka M. Chem. Rev. 1994, 94: 1375

Google Scholar
64 Knowles WS. Noyori R. Acc. Chem. Res. 2007, 40: 1238

Google Scholar
65 Noyori R. Takaya H. Acc. Chem. Res. 1990, 23: 345

Google Scholar
66a Wu J. Chen H. Kwok W. Guo RW. Zhou ZY. Yeung C. Chan ASC. J. Org. Chem. 2002, 67: 7908

Google Scholar
66b Ohkuma T. Koizumi M. Yoshida M. Noyori R. Org. Lett. 2000, 2: 1749

Google Scholar
66c Noyori R. Ohkuma T. Pure Appl. Chem. 1999, 71: 1493

Google Scholar
66d Mikami K. Korenaga T. Terada M. Ohkuma T. Pham T. Noyori R. Angew. Chem. Int. Ed. 1999, 38: 495 ; Angew. Chem. 1999, 111, 517

Google Scholar
66e Cao P. Zhang XM. J. Org. Chem. 1999, 64: 2127

Google Scholar
66f Noyori R. Doucet H. Ohkuma T. Murata K. Yokozawa T. Kozawa M. Katayama E. England AF. Ikariya T. Angew. Chem. Int. Ed. 1998, 37: 1703 ; Angew. Chem. 1995, 110, 1792

Google Scholar
66g Noyori R. Ohkuma T. Koizumi M. Doucet H. Pham T. Kozawa M. Murata K. Katayama E. Yokozawa T. Ikariya T. J. Am. Chem. Soc. 1998, 120: 13529

Google Scholar
66h Ohkuma T. Ooka H. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc. 1995, 117: 2675

Google Scholar
66i Ohkuma T. Ooka H. Ikariya T. Noyori R. J. Am. Chem. Soc. 1995, 117: 10417

Google Scholar
67 Cheemala MN. Gayral M. Brown JM. Rossen K. Knochel P. Synthesis 2007, 3877

Google Scholar
68 Dominguez B. Zanotti-Gerosa A. Hems W. Org. Lett. 2004, 6: 1927

Google Scholar
69 Messerle BA. Field LD. Vuong KQ. Turner P. Organometallics 2005, 24: 4241

Google Scholar
70a Focken T. Raabe G. Bolm C. Tetrahedron: Asymmetry 2004, 15: 1693

Google Scholar
70b Bolm C. Focken T. Raabe G. Tetrahedron: Asymmetry 2003, 14: 1733

Google Scholar
71a Trost BM. Fandrick DR. Aldrichimica Acta 2007, 40: 59

Google Scholar
71b Trost BM. Acc. Chem. Res. 2006, 39: 747

Google Scholar
71c Trost BM. J. Org. Chem. 2004, 69: 5813

Google Scholar
71d Trost BM. Crawley ML. Chem. Rev. 2003, 103: 2921

Google Scholar
71e Trost BM. VanVranken DL. Chem. Rev. 1996, 96: 395

Google Scholar
71f Trost BM. Acc. Chem. Res. 1996, 29: 355

Google Scholar
72a Whelligan DK. Bolm C. J. Org. Chem. 2006, 71: 4609

Google Scholar
72b Wu XW. Yuan K. Sun W. Zhang MJ. Hou XL. Tetrahedron: Asymmetry 2003, 14: 107

Google Scholar
73 Jiang B. Lei Y. Zhao X.-L. J. Org. Chem. 2008, 73: 7833

Google Scholar
74 Lyubimov SE. Zhuravskii RP. Rozenberg VI. Safronov AS. Petrovskii PV. Davankov VA. Russ. Chem. Bull. 2008, 57: 137

Google Scholar
75a Surry DS. Buchwald SL. Chem. Sci. 2011, 2: 57

Google Scholar
75b Surry DS. Buchwald SL. Chem. Sci. 2011, 2: 27

Google Scholar
75c Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338 ; Angew. Chem. 2008, 120, 6438

Google Scholar
76a Beller M. Schulz T. Torborg C. Schaffner B. Huang J. Zapf A. Kadyrov R. Borner A. Angew. Chem. Int. Ed. 2009, 48: 918 ; Angew. Chem. 2009, 121, 936

Google Scholar
76b Beller M. Schulz T. Torborg C. Enthaler S. Schaffner B. Dumrath A. Spannenberg A. Neumann H. Borner A. Chem. Eur. J. 2009, 15: 4528

Google Scholar
76c Sergeev AG. Schulz T. Torborg C. Spannenberg A. Neumann H. Beller M. Angew. Chem. Int. Ed. 2009, 48: 9391 ; Angew. Chem. 2009, 121, 7731

Google Scholar
76d Harkal S. Rataboul F. Zapf A. Fuhrmann C. Riermeier T. Monsees A. Beller M. Adv. Synth. Catal. 2004, 346: 1742

Google Scholar
77 Seacome RJ. Coles MP. Glover JE. Hitchcock PB. Rowlands GJ. Dalton Trans. 2010, 39: 3687

Google Scholar
78 Ruan JW. Shearer L. Mo J. Bacsa J. Zanotti-Gerosa A. Hancock F. Wu XF. Xiao JL. Org. Biomol. Chem. 2009, 7: 3236

Google Scholar
79 Hartwig JF. Inorg. Chem. 2007, 46: 1936

Google Scholar
80a Ikawa T. Barder TE. Biscoe MR. Buchwald SL. J. Am. Chem. Soc. 2007, 129: 13001

Google Scholar
80b Fujita K. Yamashita M. Puschmann F. Alvarez-Falcon MM. Incarvito CD. Hartwig JF. J. Am. Chem. Soc. 2006, 128: 9044

Google Scholar
81 Clarke ML. Konrad TM. Fuentes JA. Slawin AMZ. Angew. Chem. Int. Ed. 2010, 49: 9197 ; Angew. Chem. 2010, 122, 9383

Google Scholar
82 Hii KK. Smith AMR. Rzepa HS. White AJP. Billen D. J. Org. Chem. 2010, 75: 3085

Google Scholar
83 Falk F. Fröhlich R. Paradies J. Chem. Commun. 2011, in press; DOI: 10.1039/C1CC14844C.

Google Scholar
84a Enders D. Niemeier O. Henseler A. Chem. Rev. 2007, 107: 5606

Google Scholar
84b Enders D. Niemeier O. Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 ; Angew. Chem. 2006, 118, 1491

Google Scholar
84c Diez-Gonzalez S. Marion N. Nolan IP. Angew. Chem. Int. Ed. 2007, 46: 2988 ; Angew. Chem. 2007, 119, 3046

Google Scholar
84d Glorius F. Altenhoff G. Goddard R. Lehmann C. Chem. Commun. 2002, 2704

Google Scholar
84e Glorius F. Altenhoff G. Goddard R. Lehmann CW. Angew. Chem. Int. Ed. 2003, 42: 3690 ; Angew. Chem. 2003, 115, 3818

Google Scholar
84f Glorius F. Altenhoff G. Goddard R. Lehmann CW. J. Am. Chem. Soc. 2004, 126: 15195

Google Scholar
85 Nolan SP. Diez-Gonzalez S. Marion N. Chem. Rev. 2009, 109: 3612

Google Scholar
86a Hoveyda AH. Lee KS. Brown MK. Hird AW. J. Am. Chem. Soc. 2006, 128: 7182

Google Scholar
86b Tomioka K. Matsumoto Y. Tetrahedron Lett. 2006, 47: 5843

Google Scholar
86c Grubbs RH. Seiders TJ. Ward DW. Org. Lett. 2001, 3: 3225

Google Scholar
87 Focken T. Rudolph J. Bolm C. Synthesis 2005, 429

Google Scholar
88a Ma Q. Ma Y. Liu X. Duan W. Qu B. Song C. Tetrahedron: Asymmetry 2010, 21: 292

Google Scholar
88b Duan WZ. Ma YD. Xia HQ. Liu XY. Ma QS. Sun JS.
J. Org. Chem. 2008, 73: 4330

Google Scholar
89 Andrus MB. Ma YD. Song C. Ma CQ. Sun ZJ. Chai Q. Angew. Chem. Int. Ed. 2003, 42: 5871 ; Angew. Chem. 2003, 115, 6051

Google Scholar
90 Fürstner A. Alcarazo M. Krause H. Lehmann CW. J. Am. Chem. Soc. 2007, 129: 12676

Google Scholar
91 Fürstner A. Alcarazo M. Stork T. Anoop A. Thiel W. Angew. Chem. Int. Ed. 2010, 49: 2542 ; Angew. Chem. 2010, 122, 2596

Google Scholar
92a Krische MJ. Park H. Cho CW. J. Org. Chem. 2006, 71: 7892

Google Scholar
92b Krische MJ. Cho CW. Kong JR. Org. Lett. 2004, 6: 1337

Google Scholar
92c Krische MJ. Cho CW. Angew. Chem. Int. Ed. 2004, 43: 6689 ; Angew. Chem. 2004, 116, 6857

Google Scholar
93 Zhang T.-Z. Dai L.-X. Hou X.-L. Tetrahedron: Asymmetry 2007, 18: 1990

Google Scholar
94a Vedejs E. Duffey TA. Shaw SA. J. Am. Chem. Soc. 2009, 131: 14

Google Scholar
94b Wurz RP. Chem. Rev. 2007, 107: 5570

Google Scholar
94c Vedejs E. Shaw SA. Aleman P. Christy J. Kampf JW. Va P. J. Am. Chem. Soc. 2006, 128: 925

Google Scholar
94d Spivey AC. Arseniyadis S. Angew. Chem. Int. Ed. 2004, 43: 5436 ; Angew. Chem. 2004, 116, 5552

Google Scholar
94e Fu GC. Acc. Chem. Res. 2004, 37: 542

Google Scholar
94f Lectka T. France S. Guerin DJ. Miller SJ. Chem. Rev. 2003, 103: 2985

Google Scholar
95 De R N. Marrot J. Couty F. David ORP. Eur. J. Org. Chem. 2011, 1980

Google Scholar
96a Malkova AV. Westwater MM. Gutnov A. Ramirez-Lopez P. Friscourt F. Kadlcikova A. Hodacova J. Rankovic Z. Kotora M. Kocovsky P. Tetrahedron 2008, 64: 11335

Google Scholar
96b Kwong HL. Yeung HL. Yeung CT. Lee WS. Lee CS. Wong WL. Coord. Chem. Rev. 2007, 251: 2188

Google Scholar
97 Fulton JR. Glover JE. Kamara L. Rowlands GJ. Chem. Commun. 2011, 47: 433

Google Scholar
98 Andrus MB. Chai Q. Song C. Sun ZJ. Ma YD. Ma CQ. Dai Y. Tetrahedron Lett. 2006, 47: 8611

Google Scholar
99a Pihko PM. Hydrogen Bonding in Organic Synthesis Wiley-VCH; Weinheim: 2009.

Google Scholar
99b Schreiner PR. Chem. Soc. Rev. 2003, 32: 289

Google Scholar
100 Wenzel AG. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 12964

Google Scholar
101 Negru M. Schollmeyer D. Kunz H. Angew. Chem. Int. Ed. 2007, 46: 9339 ; Angew. Chem. 2007, 119, 9500

Google Scholar
102a Braddock DC. MacGilp ID. Perry BG. Adv. Synth. Catal. 2004, 346: 1117

Google Scholar
102b Braddock DC. MacGilp ID. Perry BG. Synlett 2003, 1121

Google Scholar
103 Hine J. Linden SM. Kanagasabapathy VM. J. Org. Chem. 1985, 50: 5096

Google Scholar
104a Zhang ZG. Schreiner PR. Chem. Soc. Rev. 2009, 38: 1187

Google Scholar
104b Connon SJ. Synlett 2009, 354

Google Scholar
104c Connon SJ. Chem. Eur. J. 2006, 12: 5418

Google Scholar
104d Taylor MS. Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 ; Angew. Chem. 2006, 116, 1550

Google Scholar
105a Schneider JF. Fröhlich R. Paradies J. Synthesis 2010, 3486

Google Scholar
105b Schneider JF. Falk FC. Fröhlich R. Paradies J. Eur. J. Org. Chem. 2010, 12: 2265

Google Scholar
106 Herrera RP. Sgarzani V. Bernardi L. Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576 ; Angew. Chem. 2008, 117, 6734

Google Scholar
107a Martin NJA. Cheng X. List B. J. Am. Chem. Soc. 2008, 130: 13862

Google Scholar
107b Martin NJA. Ozores L. List B. J. Am. Chem. Soc. 2007, 129: 8976

Google Scholar