[2.2]Paracyclophane
Derivatives: Synthesis and Application in Catalysis

doi:10.1055/s-0031-1289296

Share / Bookmark

Facebook Twitter Linkedin Google+ Weibo CiteULike

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;

Further Information

Publication History

Received 1 September 2011
Publication Date:
19 October 2011 (eFirst)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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.
1b Vögtle F. Cyclophane Chemistry Wiley; New York: 1993.
2 Hopf H. Angew. Chem. Int. Ed. 2008, 47: 9808 ; Angew. Chem. 2008, 120, 9954
3 Pye PJ. Rossen K. Reamer RA. Tsou NN. Volante RP. Reider PJ. J. Am. Chem. Soc. 1997, 119: 6207
4 Rozenberg V. Sergeeva E. Hopf H. In Modern Cyclophane Chemistry Gleiter R. Hopf H. Wiley-VCH; Weinheim: 2004. p.435-462
5 Gibson SE. Knight JD. Org. Biomol. Chem. 2003, 1: 1256
6a Hopf H. Org. Synth. 1981, 60: 41
6b Winberg HE. Fawcett FS. Org. Synth., Coll. Vol. V Wiley and Sons; New York: 1973. p.883
6c Winberg HE. Fawcett FS. Mochel WE. Theobald CW. J. Am. Chem. Soc. 1960, 82: 1428
7 Longone DT. Reetz MT. Chem. Commun. 1967, 46
8 Chow H.-F. Low K.-H. Wong KY. Synlett 2005, 2130
9 Dolbier WR. Xie P. Zhang L. Xu W. Chang Y. Abboud KA. J. Org. Chem. 2008, 73: 2469
10 Zhang L. Ogawa K. Ghiviriga I. Dolbier WR.
J. Org. Chem. 2009, 74: 6831
11 Friedmann CJ. Ay S. Bräse S. J. Org. Chem. 2010, 75: 4612
12 Rowlands GJ. Seacome RJ. Beilstein J. Org. Chem. 2009, No. 5
13a Rowlands GJ. Org. Biomol. Chem. 2008, 6: 1527
13b Hitchcock PB. Rowlands GJ. Seacome RJ. Org. Biomol. Chem. 2005, 3: 3873
14 Reich HJ. Yelm KE. J. Org. Chem. 1991, 56: 5672
15a Quesnelle C. Iihama T. Aubert T. Perrier H. Snieckus V. Tetrahedron Lett. 1992, 33: 2625
15b Snieckus V. Chem. Rev. 1990, 90: 879
16a Knochel P. Melzig L. Rauhut CB. Naredi-Rainer N. Chem. Eur. J. 2011, 17: 5361
16b Knochel P. Melzig L. Rauhut CB. Synthesis 2009, 1041
16c Knochel P. Melzig L. Rauhut CB. Chem. Commun. 2009, 3536
16d Knochel P. Rauhut CB. Melzig L. Org. Lett. 2008, 10: 3891
16e Kopp F. Sklute G. Polborn K. Marek I. Knochel P. Org. Lett. 2005, 7: 3789
17a Parmar R. Coles MP. Hitchcock PB. Rowlands GJ. Synthesis 2010, 4177
17b Hitchcock PB. Rowlands GJ. Parmar R. Chem. Commun. 2005, 4219
18 Jiang B. Zhao X.-L. Tetrahedron: Asymmetry 2004, 15: 1141
19 Zhuravsky R. Starikova Z. Vorontsov E. Rozenberg V. Tetrahedron: Asymmetry 2008, 19: 216
20 Braddock DC. MacGilp ID. Perry BG. J. Org. Chem. 2002, 67: 8679
21a Rozenberg V. Zhuravsky R. Sergeeva E. Chirality 2006, 18: 95
21b Rozenberg VI. Antonov DY. Zhuravsky RP. Vorontsov EV. Starikova ZA. Tetrahedron Lett. 2003, 44: 3801
22 Kreis M. Nieger M. Bräse S. J. Organomet. Chem. 2006, 691: 2171
23a Duthaler RO. Hafner A. Chem. Rev. 1992, 92: 807
23b Soai K. Niwa S. Chem. Rev. 1992, 92: 833
23c Rossiter BE. Swingle NM. Chem. Rev. 1992, 92: 771
24a Maruoka K. Pure Appl. Chem. 2002, 74: 123
24b Maruoka K. Ooi T. Miura T. Angew. Chem. Int. Ed. 1998, 37: 2347 ; Angew. Chem. 1998, 110, 2524
24c Lewis Acid Reagents: A Practical Approach Yamamoto H. Oxford University Press; New York: 1999.
25 Sergeeva EV. Rozenberg VI. Antonov DY. Vorontsov EV. Starikova ZA. Fedyanin IV. Hopf H. Chem. Eur. J. 2005, 11: 6944
26a Atkinson RCJ. Gibson VC. Long NJ. Chem. Soc. Rev. 2004, 33: 313
26b Colacot TJ. Chem. Rev. 2003, 103: 3101
27a Togni A. Haltermann RL. Metallocenes Wiley-VCH; Weinheim: 1998.
27b Togni A. Angew. Chem. Int. Ed. 1996, 35: 1475 ; Angew. Chem. 1996, 108, 1581
27c Togni A. Ferrocenes: Homogeneous Catalysis/Organic Synthesis/Materials Science Wiley-VCH; Weinheim: 1994.
28 Rozenberg VI. Danilova TI. Sergeeva EV. Shouklov IA. Starikova ZA. Hopf H. Kuhlein K. Eur. J. Org. Chem. 2003, 432
29 Enders D. Noll S. Raabe G. Runsink J. Synthesis 2008, 1288
30 Enders D. Noll S. Bats JW. Synlett 2005, 2679
31 Enders D. Job A. Janeck CF. Bettray W. Peters R. Tetrahedron 2002, 58: 2253
32 Bosnich B. Gavrilova AL. Chem. Rev. 2004, 104: 349
33a Gladiali S. Mroczek A. Erre G. Taras R. Tetrahedron: Asymmetry 2010, 21: 1921
33b Stoccoro S. Soro B. Minghetti G. Zucca A. Cinellu MA. Manassero M. Gladiali S. Inorg. Chim. Acta 2006, 359: 1879
33c Chelucci G. Murineddu G. Pinna GA. Tetrahedron: Asymmetry 2004, 15: 1373
33d von Zelewsky A. Mamula O. Coord. Chem. Rev. 2003, 242: 87
33e Chelucci G. Gladiali S. Sanna MG. Brunner H. Tetrahedron: Asymmetry 2000, 11: 3419
33f Bark T. Von Zelewsky A. Chimia 2000, 54: 589
33g Bolm C. Schlingloff G. Harms K. Chem. Ber. 1992, 125: 1191
33h Bolm C. Tetrahedron: Asymmetry 1991, 2: 701
34 Fu GC. Acc. Chem. Res. 2006, 39: 853
35a Wörsdörfer U. Vögtle F. Glorius F. Pfaltz A. J. Prakt. Chem. 1999, 341: 445
35b Wörsdörfer U. Vögtle F. Nieger M. Waletzke M. Grimme S. Glorius F. Pfaltz A. Synthesis 1999, 597
36 Hopf H. Aly AA. Swaminathan VN. Ernst L. Dix I. Jones PG. Eur. J. Org. Chem. 2004, 68
37 Ricci G. Ruzziconi R. Giorgio E. J. Org. Chem. 2005, 70: 1011
38 Falk H. Reichroh P. Schlögl K. Tetrahedron 1970, 26: 511
39 Pu L. Yu HB. Chem. Rev. 2001, 101: 757
40a Kozlowski MC. Fennie MW. DiMauro EF. O’brien EM. Annamalai V. Tetrahedron 2005, 61: 6249
40b Dahmen S. Bräse S. Chem. Commun. 2002, 26
40c Carreira EM. Frantz DE. Fassler R. J. Am. Chem. Soc. 2000, 122: 1806
40d Ye MC. Logaraj S. Jackman LM. Hillegass K. Hirsh KA. Bollinger AM. Grosz AL. Mani V. Tetrahedron 1994, 50: 6109
41a Rozenberg V. Danilova T. Sergeeva E. Vorontsov E. Starikova Z. Korlyukov A. Hopf H. Eur. J. Org. Chem. 2002, 468
41b Hopf H. Barrett DG. Liebigs Ann. 1995, 449
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
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
42a Dahmen S. Org. Lett. 2004, 6: 2113
42b Dahmen S. Bräse S. Org. Lett. 2001, 3: 4119
43 Höfener S. Lauterwasser F. Bräse S. Adv. Synth. Catal. 2004, 346: 755
44a Kagan HB. Girard C. Angew. Chem. Int. Ed. 1998, 37: 2923 ; Angew. Chem. 1998, 110, 3088
44b Kitamura M. Okada S. Suga S. Noyori R. J. Am. Chem. Soc. 1989, 111: 4028
45 Lauterwasser F. Vanderheiden S. Bräse S. Adv. Synth. Catal. 2006, 348: 443
46a Podlech J. Gehring T. Angew. Chem. Int. Ed. 2005, 44: 5776 ; Angew. Chem. 2005, 117, 5922
46b Bolm C. Bienewald F. Seger A. Angew. Chem. Int. Ed. 1996, 35: 1657 ; Angew. Chem. 1994, 108, 1767
46c Soai K. Hori H. Kawahara M. J. Chem. Soc., Chem. Commun. 1992, 106
46d Soai K. Niwa S. Hori H. J. Chem. Soc., Chem. Commun. 1990, 982
47 Antonov DY. Rozenberg VI. Danilova TI. Starikova ZA. Hopf H. Eur. J. Org. Chem. 2008, 1038
48 Rozenberg VI. Antonov DY. Sergeeva EV. Vorontsov EV. Starikova ZA. Fedyanin IV. Schulz C. Hopf H. Eur. J. Org. Chem. 2003, 2056
49 Bolm C. Whelligan DK. Adv. Synth. Catal. 2006, 348: 2093
50 Xin DY. Ma YD. He FY. Tetrahedron: Asymmetry 2010, 21: 333
51 Danilova TI. Rozenberg VI. Sergeeva EV. Starikova ZA. Bräse S. Tetrahedron: Asymmetry 2003, 14: 2013
52 Belokon Y. Moscalenko M. Ikonnikov N. Yashkina L. Antonov D. Vorontsov E. Rozenberg V. Tetrahedron: Asymmetry 1997, 8: 3245
53a Garcia H. Baleizao C. Chem. Rev. 2006, 106: 3987
53b Gilheany DG. McGarrigle EM. Chem. Rev. 2005, 105: 1563
54 Hosoya N. Hatayama A. Irie R. Sasaki H. Katsuki T. Tetrahedron 1994, 50: 4311
55 Shi M. Wang CJ. Tetrahedron: Asymmetry 2002, 13: 2161
56 Sawamura M. Sasaki H. Nakata T. Ito Y. Bull. Chem. Soc. Jpn. 1993, 66: 2725
57a Danilova TI. Rozenberg VI. Starikova ZA. Bräse S. Tetrahedron: Asymmetry 2004, 15: 223
57b Danilova TI. Rozenberg VI. Vorontsov EV. Starikova ZA. Hopf H. Tetrahedron: Asymmetry 2003, 14: 1375
58a Kelly BG. Gilheany DG. Tetrahedron Lett. 2002, 43: 887
58b Krause N. Hoffmann-Roder A. Synthesis 2001, 171
59 Knochel P. Perea JJA. Jones P. Tetrahedron 1998, 54: 8275
60a Sprout CM. Seto CT. J. Org. Chem. 2003, 68: 7788
60b Nugent WA. Org. Lett. 2002, 4: 2133
60c Long J. Ding KL. Angew. Chem. Int. Ed. 2001, 40: 544 ; Angew. Chem. 2001, 113, 562
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
61b Ay S. Nieger M. Bräse S. Chem. Eur. J. 2008, 14: 11539
61c Bräse S. Hoefener S. Angew. Chem. Int. Ed. 2005, 44: 7879 ; Angew. Chem. 2005, 117, 8091
62 Bräse S. Hermanns N. Dahmen S. Bolm C. Angew. Chem. Int. Ed. 2002, 41: 3692 ; Angew. Chem. 2002, 114, 3844
63 Pietrusiewicz KM. Zablocka M. Chem. Rev. 1994, 94: 1375
64 Knowles WS. Noyori R. Acc. Chem. Res. 2007, 40: 1238
65 Noyori R. Takaya H. Acc. Chem. Res. 1990, 23: 345
66a Wu J. Chen H. Kwok W. Guo RW. Zhou ZY. Yeung C. Chan ASC. J. Org. Chem. 2002, 67: 7908
66b Ohkuma T. Koizumi M. Yoshida M. Noyori R. Org. Lett. 2000, 2: 1749
66c Noyori R. Ohkuma T. Pure Appl. Chem. 1999, 71: 1493
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
66e Cao P. Zhang XM. J. Org. Chem. 1999, 64: 2127
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
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
66h Ohkuma T. Ooka H. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc. 1995, 117: 2675
66i Ohkuma T. Ooka H. Ikariya T. Noyori R. J. Am. Chem. Soc. 1995, 117: 10417
67 Cheemala MN. Gayral M. Brown JM. Rossen K. Knochel P. Synthesis 2007, 3877
68 Dominguez B. Zanotti-Gerosa A. Hems W. Org. Lett. 2004, 6: 1927
69 Messerle BA. Field LD. Vuong KQ. Turner P. Organometallics 2005, 24: 4241
70a Focken T. Raabe G. Bolm C. Tetrahedron: Asymmetry 2004, 15: 1693
70b Bolm C. Focken T. Raabe G. Tetrahedron: Asymmetry 2003, 14: 1733
71a Trost BM. Fandrick DR. Aldrichimica Acta 2007, 40: 59
71b Trost BM. Acc. Chem. Res. 2006, 39: 747
71c Trost BM. J. Org. Chem. 2004, 69: 5813
71d Trost BM. Crawley ML. Chem. Rev. 2003, 103: 2921
71e Trost BM. VanVranken DL. Chem. Rev. 1996, 96: 395
71f Trost BM. Acc. Chem. Res. 1996, 29: 355
72a Whelligan DK. Bolm C. J. Org. Chem. 2006, 71: 4609
72b Wu XW. Yuan K. Sun W. Zhang MJ. Hou XL. Tetrahedron: Asymmetry 2003, 14: 107
73 Jiang B. Lei Y. Zhao X.-L. J. Org. Chem. 2008, 73: 7833
74 Lyubimov SE. Zhuravskii RP. Rozenberg VI. Safronov AS. Petrovskii PV. Davankov VA. Russ. Chem. Bull. 2008, 57: 137
75a Surry DS. Buchwald SL. Chem. Sci. 2011, 2: 57
75b Surry DS. Buchwald SL. Chem. Sci. 2011, 2: 27
75c Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338 ; Angew. Chem. 2008, 120, 6438
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
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
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
76d Harkal S. Rataboul F. Zapf A. Fuhrmann C. Riermeier T. Monsees A. Beller M. Adv. Synth. Catal. 2004, 346: 1742
77 Seacome RJ. Coles MP. Glover JE. Hitchcock PB. Rowlands GJ. Dalton Trans. 2010, 39: 3687
78 Ruan JW. Shearer L. Mo J. Bacsa J. Zanotti-Gerosa A. Hancock F. Wu XF. Xiao JL. Org. Biomol. Chem. 2009, 7: 3236
79 Hartwig JF. Inorg. Chem. 2007, 46: 1936
80a Ikawa T. Barder TE. Biscoe MR. Buchwald SL. J. Am. Chem. Soc. 2007, 129: 13001
80b Fujita K. Yamashita M. Puschmann F. Alvarez-Falcon MM. Incarvito CD. Hartwig JF. J. Am. Chem. Soc. 2006, 128: 9044
81 Clarke ML. Konrad TM. Fuentes JA. Slawin AMZ. Angew. Chem. Int. Ed. 2010, 49: 9197 ; Angew. Chem. 2010, 122, 9383
82 Hii KK. Smith AMR. Rzepa HS. White AJP. Billen D. J. Org. Chem. 2010, 75: 3085
83 Falk F. Fröhlich R. Paradies J. Chem. Commun. 2011, in press; DOI: 10.1039/C1CC14844C.
84a Enders D. Niemeier O. Henseler A. Chem. Rev. 2007, 107: 5606
84b Enders D. Niemeier O. Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 ; Angew. Chem. 2006, 118, 1491
84c Diez-Gonzalez S. Marion N. Nolan IP. Angew. Chem. Int. Ed. 2007, 46: 2988 ; Angew. Chem. 2007, 119, 3046
84d Glorius F. Altenhoff G. Goddard R. Lehmann C. Chem. Commun. 2002, 2704
84e Glorius F. Altenhoff G. Goddard R. Lehmann CW. Angew. Chem. Int. Ed. 2003, 42: 3690 ; Angew. Chem. 2003, 115, 3818
84f Glorius F. Altenhoff G. Goddard R. Lehmann CW. J. Am. Chem. Soc. 2004, 126: 15195
85 Nolan SP. Diez-Gonzalez S. Marion N. Chem. Rev. 2009, 109: 3612
86a Hoveyda AH. Lee KS. Brown MK. Hird AW. J. Am. Chem. Soc. 2006, 128: 7182
86b Tomioka K. Matsumoto Y. Tetrahedron Lett. 2006, 47: 5843
86c Grubbs RH. Seiders TJ. Ward DW. Org. Lett. 2001, 3: 3225
87 Focken T. Rudolph J. Bolm C. Synthesis 2005, 429
88a Ma Q. Ma Y. Liu X. Duan W. Qu B. Song C. Tetrahedron: Asymmetry 2010, 21: 292
88b Duan WZ. Ma YD. Xia HQ. Liu XY. Ma QS. Sun JS.
J. Org. Chem. 2008, 73: 4330
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
90 Fürstner A. Alcarazo M. Krause H. Lehmann CW. J. Am. Chem. Soc. 2007, 129: 12676
91 Fürstner A. Alcarazo M. Stork T. Anoop A. Thiel W. Angew. Chem. Int. Ed. 2010, 49: 2542 ; Angew. Chem. 2010, 122, 2596
92a Krische MJ. Park H. Cho CW. J. Org. Chem. 2006, 71: 7892
92b Krische MJ. Cho CW. Kong JR. Org. Lett. 2004, 6: 1337
92c Krische MJ. Cho CW. Angew. Chem. Int. Ed. 2004, 43: 6689 ; Angew. Chem. 2004, 116, 6857
93 Zhang T.-Z. Dai L.-X. Hou X.-L. Tetrahedron: Asymmetry 2007, 18: 1990
94a Vedejs E. Duffey TA. Shaw SA. J. Am. Chem. Soc. 2009, 131: 14
94b Wurz RP. Chem. Rev. 2007, 107: 5570
94c Vedejs E. Shaw SA. Aleman P. Christy J. Kampf JW. Va P. J. Am. Chem. Soc. 2006, 128: 925
94d Spivey AC. Arseniyadis S. Angew. Chem. Int. Ed. 2004, 43: 5436 ; Angew. Chem. 2004, 116, 5552
94e Fu GC. Acc. Chem. Res. 2004, 37: 542
94f Lectka T. France S. Guerin DJ. Miller SJ. Chem. Rev. 2003, 103: 2985
95 De R N. Marrot J. Couty F. David ORP. Eur. J. Org. Chem. 2011, 1980
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
96b Kwong HL. Yeung HL. Yeung CT. Lee WS. Lee CS. Wong WL. Coord. Chem. Rev. 2007, 251: 2188
97 Fulton JR. Glover JE. Kamara L. Rowlands GJ. Chem. Commun. 2011, 47: 433
98 Andrus MB. Chai Q. Song C. Sun ZJ. Ma YD. Ma CQ. Dai Y. Tetrahedron Lett. 2006, 47: 8611
99a Pihko PM. Hydrogen Bonding in Organic Synthesis Wiley-VCH; Weinheim: 2009.
99b Schreiner PR. Chem. Soc. Rev. 2003, 32: 289
100 Wenzel AG. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 12964
101 Negru M. Schollmeyer D. Kunz H. Angew. Chem. Int. Ed. 2007, 46: 9339 ; Angew. Chem. 2007, 119, 9500
102a Braddock DC. MacGilp ID. Perry BG. Adv. Synth. Catal. 2004, 346: 1117
102b Braddock DC. MacGilp ID. Perry BG. Synlett 2003, 1121
103 Hine J. Linden SM. Kanagasabapathy VM. J. Org. Chem. 1985, 50: 5096
104a Zhang ZG. Schreiner PR. Chem. Soc. Rev. 2009, 38: 1187
104b Connon SJ. Synlett 2009, 354
104c Connon SJ. Chem. Eur. J. 2006, 12: 5418
104d Taylor MS. Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 ; Angew. Chem. 2006, 116, 1550
105a Schneider JF. Fröhlich R. Paradies J. Synthesis 2010, 3486
105b Schneider JF. Falk FC. Fröhlich R. Paradies J. Eur. J. Org. Chem. 2010, 12: 2265
106 Herrera RP. Sgarzani V. Bernardi L. Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576 ; Angew. Chem. 2008, 117, 6734
107a Martin NJA. Cheng X. List B. J. Am. Chem. Soc. 2008, 130: 13862
107b Martin NJA. Ozores L. List B. J. Am. Chem. Soc. 2007, 129: 8976