Organocatalytic Formation of
Quaternary Stereocenters

Marco Bella; Tecla Gasperi

doi:10.1055/s-0029-1216796

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Synthesis 2009(10): 1583-1614
DOI: 10.1055/s-0029-1216796

REVIEW

Organocatalytic Formation of Quaternary Stereocenters

Marco Bella*, Tecla Gasperi
Dipartimento di Chimica and Istituto di Chimica Biomolecolare, ‘Sapienza’ Università di Roma, P.le Aldo Moro 5, 00185 Roma, Italy
Fax: +39(06)490631; e-Mail: Marco.Bella@uniroma1.it;

Further Information

Publication History

Received 27 February 2009
Publication Date:
04 May 2009 (online)

Abstract
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Abstract

This work reviews the authors’ choice of recently published papers where at least one asymmetric quaternary stereocenter has been formed via organocatalysis. The scope and limitations of the reactions are highlighted.

1 Introduction

2 Alkylation and Arylation Reactions

3 Addition to Carbon-Carbon Multiple Bonds

4 Addition to N=X Double Bonds

5 Nucleophilic Aziridine-Ring Opening

6 Aldol and Related Reactions

7 Brønsted Acid Organocatalyzed Formation of Nitrogen-Containing Quaternary Stereocenters

8 Halogenation and Pseudohalogenation Reactions

9 Epoxidation

10 Diels-Alder Reaction

11 N-Heterocyclic Carbene Catalysis

12 Cascade Reactions

13 Conclusion and Outlook

Key words

alkaloids - amino acids - asymmetric catalysis - carbenes - Michael additions

References

Selected examples where quaternary center formation was crucial in a natural product total synthesis: Cyclotryptamine alkaloids:
2a Steven A. Overman LE. Angew. Chem. Int. Ed. 2007, 46: 5488

Google Scholar
Azadirachtin:
2b Veitch GE. Beckmann E. Burke BJ. Boyer A. Ayats C. Ley SV. Angew. Chem. Int. Ed. 2007, 46: 7633

Google Scholar
Diazonamide A:
2c Burgett AWG. Li Q. Wei Q. Harran PG. Angew. Chem. Int. Ed. 2003, 42: 4961

Google Scholar
2d Nicolaou KC. Rao PB. Hao J. Reddy MV. Rassias G. Huang X. Chen DY.-K. Snyder SA. Angew. Chem. Int. Ed. 2003, 42: 1753

Google Scholar
2e Nicolaou KC. Bella M. Chen DY.-K. Huang X. Ling T. Snyder SA. Angew. Chem. Int. Ed. 2002, 41: 3495

Google Scholar
3a Cozzi PG. Hilgraf R. Zimmermann N. Eur. J. Org. Chem. 2007, 5969

Google Scholar
3b Trost BM. Jiang C. Synthesis 2006, 369

Google Scholar
3c Christoffers J. Baro A. Adv. Synth. Catal. 2005, 347: 1473

Google Scholar
3d Quaternary Stereocenters - Challenges and Solutions for Organic Synthesis Christoffers J. Baro A. Wiley-VCH; Weinheim: 2005.

Google Scholar
3e Peterson EA. Overman LE. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 11943

Google Scholar
3f Douglas CJ. Overman LE. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5363

Google Scholar
3g Ramon DJ. Yus M. Curr. Org. Chem. 2004, 8: 149

Google Scholar
3h Denissova I. Barriault L. Tetrahedron 2003, 59: 10105

Google Scholar
3i Christoffers J. Mann A. Angew. Chem. Int. Ed. 2001, 40: 4591

Google Scholar
3j Corey EJ. Guzman-Perez A. Angew. Chem. Int. Ed. 1998, 37: 389

Google Scholar
3k Fuji K. Chem. Rev. 1993, 93: 2037

Google Scholar
3l Martin SF. Tetrahedron 1980, 36: 419

Google Scholar
4 Wang X. Kitamura M. Maruoka KM. J. Am. Chem. Soc. 2007, 129: 1038

Crossref PubMed Google Scholar
5 Marcia de Figueiredo RM. Christmann M. Eur. J. Org. Chem. 2007, 2575

Crossref Google Scholar
6a Use and derivatization of cinchona alkaloids: Kacprzak K. Gawronski J. Synthesis 2001, 961

Google Scholar
6b Tian S.-K. Chen Y. Hang J. Tang L. McDaid P. Deng L. Acc. Chem. Res. 2004, 37: 621

Google Scholar
6c Marcelli T. van Maarseveen JH. Hiemstra H. Angew. Chem. Int. Ed. 2006, 45: 7496

Google Scholar
6d Leow D. Tan C.-H. Chem. Asian J. 2009, 4: 488

Google Scholar
7a Hashimoto T. Maruoka K. Chem. Rev. 2007, 107: 5656

Google Scholar
7b Ooi T. Maruoka K. Angew. Chem. Int. Ed. 2007, 46: 4222

Google Scholar
8 Hajos ZG. Parrish DR. J. Org. Chem. 1974, 39: 1615

Crossref Google Scholar
9 Notz W. Tanaka F. Barbas CF. Acc. Chem. Res. 2004, 37: 580

Crossref PubMed Google Scholar
10 Adair G. Mukherjee S. List B. Aldrichimica Acta 2008, 41: 31

Google Scholar
11a Enders D. Balensiefer T. Acc. Chem. Res. 2004, 37: 534

Google Scholar
11b Enders D. Niemeier O. Henseler A. Chem. Rev. 2007, 107: 5606

Google Scholar
12 Bella M. Scarpino Schietroma DM. Cusella PP. Gasperi T. Visca V. Chem. Commun. 2009, 597

Crossref Google Scholar
13 Dolling U.-H. Davis P. Grabowsky EJJ. J. Am. Chem. Soc. 1984, 106: 446

Crossref Google Scholar
14 Ooi T. Takeuchi M. Kamada M. Maruoka K. J. Am. Chem. Soc. 2000, 122: 5228

Crossref Google Scholar
15 Bella M. Kobbelgaard S. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 3670

Crossref PubMed Google Scholar
16a Maruoka K. Ooi T. Chem. Rev. 2003, 103: 3013

Google Scholar
16b Enantioselective Organocatalysis Dalko PI. Wiley-VCH; Weinheim: 2007.

Google Scholar
16c Berkessel A. Gröger H. Asymmetric Organocatalysis Wiley-VCH; Weinheim: 2004.

Google Scholar
17 Wynberg H. Helder R. Tetrahedron Lett. 1975, 46: 4057

Google Scholar
18a Hughes DL. Dolling U.-H. Ryan KM. Schoenewaldt EF. Grabowsky EJJ. J. Org. Chem. 1987, 52: 4745

Google Scholar
18b Lipkowitz KB. Cavenaugh MW. Baker B. O’Donnell MJ. J. Org. Chem. 1991, 56: 5181

Google Scholar
19 See: Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc. 1997, 119: 12414

Crossref Google Scholar
20a Lygo B. Wainwright PG. Tetrahedron Lett. 1998, 39: 1599

Google Scholar
20b Corey EJ. Zhang FY. Org. Lett. 1999, 1: 1287

Google Scholar
20c Ooi T. Ohara D. Tamura M. Maruoka K. J. Am. Chem. Soc. 2004, 126: 6844

Google Scholar
21 Chen Z. Zhu G. Jiang Q. Xiao D. Cao P. Zhang X. J. Org. Chem. 1998, 63: 5631

Crossref Google Scholar
22 For organocatalysis by phosphines, see: Methhot JL. Roush WR. Adv. Synth. Catal. 2004, 346: 1035

Crossref Google Scholar
23 Brandes S. Niess B. Bella M. Prieto A. Overgaard J. Jørgensen KA. Chem. Eur. J. 2006, 12: 6039

Crossref PubMed Google Scholar
24 Ooi T. Miki T. Taniguchi M. Shiraishi M. Takeuchi M. Maruoka K. Angew. Chem. Int. Ed. 2003, 42: 3796

Crossref PubMed Google Scholar
25 Wu F. Hong R. Khan J. Liu X. Deng L. Angew. Chem. Int. Ed. 2006, 45: 4301

Crossref Google Scholar
26 Wu F. Li H. Hong R. Deng L. Angew. Chem. Int. Ed. 2006, 45: 947

Crossref Google Scholar
27 Hermann K. Wynberg H. J. Org. Chem. 1979, 44: 2238

Crossref Google Scholar
28 Conn RSE. Lovell AV. Karady S. Weinstrock LM. J. Org. Chem. 1986, 51: 4710

Crossref Google Scholar
29 Liu T.-Y. Li R. Chai Q. Long J. Wu Y. Ding L.-S. Chen Y.-C. Chem. Eur. J. 2007, 13: 319

Crossref PubMed Google Scholar
30 Li H. Song J. Liu X. Deng L. J. Am. Chem. Soc. 2005, 127: 8948

Crossref PubMed Google Scholar
31 Capuzzi M. Perdicchia D. Jørgensen KA. Chem. Eur. J. 2008, 14: 128

Crossref Google Scholar
32 Wang B. Wu F. Wang Y. Liu X. Deng L. J. Am. Chem. Soc. 2007, 129: 768

Crossref PubMed Google Scholar
33 Bella M. Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 5672

Crossref PubMed Google Scholar
34 Li H. Wang Y. Tang L. Wu F. Liu X. Guo C. Foxman BM. Deng L. Angew. Chem. Int. Ed. 2005, 44: 105

Crossref PubMed Google Scholar
35 Hynes PS. Stranges D. Stupple PA. Guarna A. Dixon DJ. Org. Lett. 2007, 9: 2107

Crossref PubMed Google Scholar
36 Bartoli G. Bosco M. Carlone A. Cavalli A. Locatelli M. Mazzanti A. Ricci P. Sambri L. Melchiorre P. Angew. Chem. Int. Ed. 2006, 45: 4966

Crossref Google Scholar
37 Wang Y. Liu X. Deng L. J. Am. Chem. Soc. 2006, 128: 3928

Crossref Google Scholar
38 Poulsen TB. Bernardi L. Alemán J. Overgaard J. Jørgensen KA. J. Am. Chem. Soc. 2007, 129: 441

Crossref PubMed Google Scholar
39 Poulsen TB. Bernardi L. Bell M. Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 6551

Crossref Google Scholar
40 Bernardi L. Cantarero JL. Niess B. Jørgensen KA. J. Am. Chem. Soc. 2007, 129: 5772

Crossref PubMed Google Scholar
41a Aléman J. Cabrera S. Maerten E. Overgaard J. Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 5520

Google Scholar
41b Aléman J. Richter B. Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 5515

Google Scholar
42a Poulsen TB. Alemparte C. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 11614

Google Scholar
42b Poulsen TB. Bell M. Jørgensen KA. Org. Biomol. Chem. 2006, 63

Google Scholar
43 Bell M. Frish K. Jørgensen KA. J. Org. Chem. 2006, 71: 5407

Crossref PubMed Google Scholar
44 van Steenis DJVC. Marcelli T. Lutz M. Spek AL. van Maareseveen JH. Hiemstra H. Adv. Synth. Catal. 2007, 349: 281

Crossref Google Scholar
45a Melchiorre P. Jørgensen KA. J. Org. Chem. 2003, 68: 4151

Google Scholar
45b Chi Y. Gellman SH. Org. Lett. 2005, 7: 4253

Google Scholar
45c Peelen TJ. Chi Y. G ellman SH. J. Am. Chem. Soc. 2005, 127: 11598

Google Scholar
46 See for example: Desmaële D. Mekouar K. D’Angelo J. J. Org. Chem. 1997, 62: 3890

Crossref Google Scholar
47 Mase N. Thayumanavan R. Tanaka F. Barbas CF. Org. Lett. 2004, 6: 2527

Crossref PubMed Google Scholar
48 Genet J.-P. Greck C. Lavergne CD. In Modern Amination Methods Ricci A. Wiley-VCH; Weinheim: 2000. Chap. 3.

Google Scholar
49a List B. J. Am. Chem. Soc. 2002, 124: 5656

Google Scholar
49b Kumaragurubaran N. Juhl K. Zhuang W. Bogevig A. Jørgensen KA. J. Am. Chem. Soc. 2002, 124: 6254

Google Scholar
49c Bogevig A. Juhl K. Kumaragurubaran N. Zhuang W. Jørgensen KA. Angew. Chem. Int. Ed. 2002, 41: 1790

Google Scholar
50 Chowdari NS. Barbas CF. Org. Lett. 2005, 7: 867

Crossref PubMed Google Scholar
51 Almquist RG. Chao W.-R. White C. J. Med. Chem. 1985, 28: 1067

Crossref Google Scholar
52 Suri J. Steiner DD. Barbas CF. Org. Lett. 2005, 7: 3885

Crossref PubMed Google Scholar
53a Baumann T. Vogt H. Bräse S. Eur. J. Org. Chem. 2007, 266

Google Scholar
53b Baumann T. Bächle M. Hartmann C. Bräse S. Eur. J. Org. Chem. 2008, 2207

Google Scholar
54a Marigo M. Kumaragurubaran N. Jørgensen KA. Synthesis 2005, 957

Google Scholar
54b Marigo M. Juhl K. Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 1367

Google Scholar
54c Juhl K. Jørgensen KA. J. Am. Chem. Soc. 2002, 124: 2420

Google Scholar
55 Saaby S. Bella M. Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 8120

Crossref Google Scholar
56a Pihko PM. Pohjakallio A. Synlett 2004, 2118

Google Scholar
56b Liu X. Li H. Deng L. Org. Lett. 2005, 7: 167

Google Scholar
57 Terada M. Nakano M. Ube H. J. Am. Chem. Soc. 2006, 128: 16044

Crossref Google Scholar
58 Lopez-Cantarero J. Cid MB. Poulsen TB. Bella M. Ruano JLG. Jørgensen KA. J. Org. Chem. 2007, 72: 7062

Crossref Google Scholar
59a List B. Pojarliev P. Biller WT. Martin H. J. Am. Chem. Soc. 2002, 124: 827

Google Scholar
59b Enders D. Grondal C. Vrettou M. Raabe G. Angew. Chem. Int. Ed. 2005, 44: 4079

Google Scholar
59c Enders D. Palecek J. Grondal C. Chem. Commun. 2006, 655

Google Scholar
59d Enders D. Vrettou M. Synthesis 2006, 2155

Google Scholar
60 Zhuang W. Saaby S. Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 4476

Crossref Google Scholar
61 Chowdary NS. Suri TJ. Barbas CF. Org. Lett. 2004, 6: 2507

Crossref Google Scholar
For recent reviews, see:
62a Verkade JMM. van Hemert LJC. Quaedflieg PJLM. Rutjes FPJT. Chem. Soc. Rev. 2008, 37: 29

Google Scholar
62b Ting A. Schaus SC. Eur. J. Org. Chem. 2007, 5797

Google Scholar
63 Sukach VA. Golvach NM. Pirozhenko VV. Rusanov EB. Vovk MV. Tetrahedron: Asymmetry 2008, 19: 761

Crossref Google Scholar
64 Yamoaka YY. Miyabe H. Yasui Y. Takemoto Y. Synthesis 2007, 2571

Article in Thieme Connect Google Scholar
65a Song J. Wang Y. Deng L. J. Am. Chem. Soc. 2006, 128: 6048

Google Scholar
65b Tillman AL. Ye J. Dixon DJ. Chem. Commun. 2006, 1191

Google Scholar
66 Tian X. Jiang K. Peng J. Du W. Chen Y.-C. Org. Lett. 2008, 10: 3583

Crossref Google Scholar
67 Han B. Liu Q.-P. Li R. Tian X. Xiong X.-F. Deng J.-G. Chen Y.-C. Chem. Eur. J. 2008, 14: 8094

Crossref Google Scholar
68 Poulsen TB. Alemparte C. Saaby S. Bella M. Jørgensen KA. Angew. Chem. Int. Ed. 2005, 44: 2896

Crossref PubMed Google Scholar
69 Marianacci O. Micheletti G. Bernardi L. Fini F. Fochi M. Pettersen D. Sgarzani V. Ricci A. Chem. Eur. J. 2007, 13: 8338

Crossref Google Scholar
70 Hatano M. Maki T. Moriyama K. Arinobe M. Ishihara K. J. Am. Chem. Soc. 2008, 130: 16858

Crossref Google Scholar
71 Strecker A. Justus Liebigs Ann. Chem. 1850, 75: 27

Crossref Google Scholar
72a Ishitani H. Komiyama S. Kobayashi S. Angew Chem. Int. Ed. 1998, 37: 3186

Google Scholar
72b Krueger CA. Kuntz KW. Dzierba CD. Wirschun WG. Gleason JD. Snapper ML. Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 4284

Google Scholar
72c Corey EJ. Grogan MJ. Org. Lett. 1999, 1: 157

Google Scholar
72d Sigman MS. Vachal P. Jacobsen EN. Angew. Chem. Int. Ed. 2000, 39: 1279

Google Scholar
73a Vachal P. Jacobsen EN. Org. Lett. 2000, 2: 867

Google Scholar
73b Vachal P. Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 10012

Google Scholar
74 Gröger H. Chem. Rev. 2003, 103: 2795

Crossref Google Scholar
75a Huang X. Huang J. Wen Y. Feng X. Adv. Synth. Catal. 2006, 348: 2579

Google Scholar
75b Hou Z. Wang J. Liu X. Feng X. Chem. Eur. J. 2008, 14: 4484

Google Scholar
76 Becker C. Hoben C. Kunz H. Adv. Synth. Catal. 2007, 349: 417

Crossref Google Scholar
77a Moss TA. Fenwick DR. Dixon DJ. J. Am. Chem. Soc. 2008, 130: 10076

Google Scholar
77b Paixão MW. Nielsen M. Jacobsen CB. Jørgensen KA. Org. Biomol. Chem. 2008, 3467

Google Scholar
78 Pulkkinen J. Aburel PS. Halland N. Jørgensen KA. Adv. Synth. Catal. 2004, 346: 1077

Crossref Google Scholar
79 Wang XJ. Zhao Y. Liu J.-T. Org. Lett. 2007, 9: 1343

Crossref Google Scholar
80 Zhuang W. Gathergood N. Hazell RG. Jørgensen KA. J. Org. Chem. 2001, 66: 1009

Crossref Google Scholar
81 Lyle MPA. Draper ND. Wilson PD. Org. Lett. 2005, 7: 901

Crossref Google Scholar
82 Török B. Abid M. London G. Esquibel J. Török M. Mhadgut SC. Yan P. Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086

Crossref PubMed Google Scholar
83 Li H. Wang Y.-Q. Deng L. Org. Lett. 2006, 8: 4063

Crossref Google Scholar
84 Rueping M. Theissmann T. Kuenkel A. Koenigs RM. Angew. Chem. Int. Ed. 2008, 47: 6798

Crossref PubMed Google Scholar
85a Luppi G. Cozzi PG. Monari M. Kaptein AB. Broxterman SJ. Tomasini C. J. Org. Chem. 2005, 70: 7418
85b Luppi G. Monari M. Corréa RJ. Violante FA. Pinto B. Kaptein AB. Broxterman SJ. Tomasini C. Tetrahedron 2006, 62: 12017
86 Malkov AV. Kabeshov MA. Bella M. Kysilka O. Malyshev DA. Pluhackova K. Kocovsky P. Org. Lett. 2007, 9: 5473

Crossref PubMed Google Scholar
87 Nakamura S. Hara N. Nakashima H. Kubo K. Shibata N. Toru T. Chem. Eur. J. 2008, 14: 8079

Crossref PubMed Google Scholar
88 Chen X. Wang J. Zhu Y. Shang D. Gao B. Liu X. Feng X. Su Z. Hu C. Chem. Eur. J. 2008, 14: 10896

Crossref Google Scholar
89 Sano D. Nagata K. Itoh T. Org. Lett. 2008, 10: 1593

Crossref Google Scholar
Earliest studies in organocatalysis:
90a List B. Lerner RA. Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395

Google Scholar
90b Sakhtivel K. Notz W. Bui T. Barbas CF. J. Am. Chem. Soc. 2001, 123: 5260

Google Scholar
90c Cordova A. Notz W. Bui T. Barbas CF. J. Org. Chem. 2002, 67: 301

Google Scholar
90d Northrup AB. MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 6798

Google Scholar
90e Tang Z. Jiang F. Yu L.-T. Cui X. Gong LZ. Quiao A. Jiang Y.-Z. Wu Y.-D. J. Am. Chem. Soc. 2003, 125: 5262

Google Scholar
90f Pidathala C. Hoang L. Vignola N. List B. Angew. Chem. Int. Ed. 2003, 42: 2785

Google Scholar
90g Juhl K. Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 1498

Google Scholar
90h Halland N. Aburel PS. Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 661

Google Scholar
90i Hoang L. Bahmanyar S. Houk KN. Martin H. List B. J. Am. Chem. Soc. 2003, 125: 16

Google Scholar
90j Bahmanyar S. Houk KN. List B. J. Am. Chem. Soc. 2003, 125: 2475

Google Scholar
91 Bøgevig A. Nagaswamy K. Jørgensen KA. Chem. Commun. 2002, 620

Crossref Google Scholar
92 Tokuda O. Kano T. Gao W.-G. Ikemoto T. Maruoka K. Org. Lett. 2005, 7: 5103

Crossref Google Scholar
93 Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl. 1971, 10: 496

Crossref Google Scholar
94 Enders D. Niemeier O. Straver L. Synlett 2006, 3399

Article in Thieme Connect Google Scholar
95 Zheng C. Wu Y. Wang X. Zhao G. Adv. Synth. Catal. 2008, 350: 2690

Crossref Google Scholar
96 Yoshitomi Y. Makino K. Hamada Y. Org. Lett. 2007, 9: 2457

Crossref PubMed Google Scholar
97a Halland N. Hazell RG. Jørgensen KA. J. Org. Chem. 2002, 67: 8331

Google Scholar
97b Betancort JM. Barbas CF. Org. Lett. 2001, 3: 3737

Google Scholar
98a Mase N. Tanaka F. Barbas CF. Org. Lett. 2003, 5: 4369

Google Scholar
98b Mase N. Tanaka F. Barbas CF. Angew. Chem. Int. Ed. 2004, 43: 2420

Google Scholar
99 Dambruso P. Massi A. Dondoni A. Org. Lett. 2005, 7: 4657

Crossref Google Scholar
100 Sampak S. Zhao C.-G. J. Am. Chem. Soc. 2006, 128: 7442

Crossref PubMed Google Scholar
101 Tang Z. Cun L.-F. Cui X. Mi A.-Q. Jiang Y.-Z. Gong L.-Z. Org. Lett. 2006, 6: 1263

Google Scholar
102 Jia Y.-X. Zhong J. Zhu S.-F. Zhang C.-M. Zhou Q.-L. Angew. Chem. Int. Ed. 2007, 46: 5565

Crossref Google Scholar
103 For an asymmetric fluorination of β-keto esters, see: Hintermann L. Togni A. Angew. Chem. Int. Ed. 2005, 39: 4359

Google Scholar
104 Cahard D. Audouard C. Plaquevent J.-C. Roques N. Org. Lett. 2000, 2: 3699

Crossref Google Scholar
105 Marigo M. Fielenbach D. Braunton A. Kjærsgaard A. Jørgensen KA. Angew. Chem. Int. Ed. 2005, 44: 3703

Crossref Google Scholar
106 Enders D. Hüttl MRM. Synlett 2005, 991

Article in Thieme Connect Google Scholar
107a Beeson TD. MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 8826

Google Scholar
107b Steiner DD. Mase N. Barbas CF. Angew. Chem. Int. Ed. 2005, 44: 3706

Google Scholar
108 Shibatomi K. Yamamoto H. Angew. Chem. Int. Ed. 2008, 47: 5796

Crossref PubMed Google Scholar
109 Bartoli G. Bosco M. Carlone A. Locatelli M. Melchiorre P. Sambri L. Angew. Chem. Int. Ed. 2005, 44: 6219

Crossref Google Scholar
110 Sobhani S. Fielenbach D. Marigo M. Wabnitz TC. Jørgensen KA. Chem. Eur. J. 2005, 11: 5689

Crossref Google Scholar
111a Tu Y. Wang ZX. Shi Y. J. Am. Chem. Soc. 1996, 118: 9806

Google Scholar
111b Wang ZX. Tu Y. Frohn M. Zhang JR. Shi Y. J. Am. Chem. Soc. 1997, 119: 11224

Google Scholar
111c Shi Y. Acc. Chem. Res. 2004, 37: 488

Google Scholar
112 Hanquet G. Lusinchi X. Millet P. Tetrahedron Lett. 1988, 29: 3941

Crossref Google Scholar
113 Aggarwal VK. Wang MF. Chem. Commun. 1996, 191

Crossref Google Scholar
114 Page PCB. Buckley BR. Blaker AJ. Org. Lett. 2004, 6: 1543

Crossref Google Scholar
115a Adamo MFA. Aggarwal VK. Sage MA. J. Am. Chem. Soc. 2002, 124: 11223

Google Scholar
115b Adamo MFA. Aggarwal VK. Sage MA. J. Am. Chem. Soc. 2000, 122: 8317

Google Scholar
115c Aggarwal VK. Lopin C. Sandrinelli F. J. Am. Chem. Soc. 2003, 123: 7596

Google Scholar
116 Peris G. Jakobsche CE. Miller S. J. Am. Chem. Soc. 2007, 129: 8710

Crossref Google Scholar
117 Berkessel A. Angew. Chem. Int. Ed. 2008, 47: 3677

Crossref Google Scholar
118 Wu XY. She XG. Shi YA. J. Am. Chem. Soc. 2002, 124: 8792

Crossref Google Scholar
119 Marigo M. Franzen J. Poulsen TB. Zhuang W. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 6964

Crossref PubMed Google Scholar
120 Zhuang W. Marigo M. Jørgensen KA. Org. Biomol. Chem. 2005, 3883

Crossref Google Scholar
121 Ahrendt KA. Borths CJ. MacMillan DWC. J. Am. Chem. Soc. 2000, 122: 4243

Crossref Google Scholar
122 Kinsman AC. Kerr MA. J. Am. Chem. Soc. 2003, 125: 14120

Crossref Google Scholar
123 Ishihara K. Nakano K. J. Am. Chem. Soc. 2005, 127: 10504

Crossref PubMed Google Scholar
124 Ishihara K. Nakano K. Akakura M. Org. Lett. 2008, 10: 2893

Crossref Google Scholar
125 Northrup AB. MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 2458

Crossref PubMed Google Scholar
126 Huang Y. Rawal VH. J. Am. Chem. Soc. 2002, 124: 9962

Crossref Google Scholar
127 Thadani AN. Stankovic AR. Rawal VH. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5846

Crossref Google Scholar
128a Shuster T. Bauch M. Dürner G. Göbel MW. Org. Lett. 2000, 2: 179

Google Scholar
128b Tsogoeva SB. Dürner G. Bolte M. Göbel MW. Eur. J. Org. Chem. 2003, 1661

Google Scholar
129 Akalay D. Dürner G. Göbel MW. Eur. J. Org. Chem. 2008, 2365

Crossref Google Scholar
130 Ukai T. Tanaka R. Dokawa T. J. Pharm. Soc. Jpn. 1943, 63: 296

Google Scholar
131 Breslow R. J. Am. Chem. Soc. 1958, 80: 3719

Google Scholar
132a Enders D. Breuer K. Teles JH. Helv. Chim. Acta 1996, 79: 1217

Google Scholar
132b Enders D. Breuer K. In Comprehensive Asymmetric Catalysis Vol. 3: Jacobsen E. N. Pfalz A. Yamamoto H. Springer; Heidelberg: 1999. p.1093

Google Scholar
132c Teles JH. Breuer K. Enders D. Gielen H. Synth. Commun. 1999, 29: 1

Google Scholar
132d Enders D. Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743

Google Scholar
133a Knight RL. Leeper FJ. Tetrahedron Lett. 1997, 38: 3611

Google Scholar
133b Gerhards A. Leeper FJ. Tetrahedron Lett. 1997, 38: 3615

Google Scholar
134a Stetter H. Angew. Chem. Int. Ed. 1976, 15: 639

Google Scholar
134b Hachisu Y. Bode JW. Suzuki K. J. Am. Chem. Soc. 2003, 125: 8432

Google Scholar
135a Enders D. Niemeier O. Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463

Google Scholar
135b Enders D. Niemeier O. Raabe G. Synlett 2006, 2431

Google Scholar
136 Enders D. Breuer K. Helv. Chim. Acta 1996, 79: 1899

Google Scholar
137a Kerr MS. Rovis T. J. Am. Chem. Soc. 2004, 126: 8876

Google Scholar
137b de Alaniz JR. Rovis T. J. Am. Chem. Soc. 2005, 127: 6284

Google Scholar
138a Sohn SS. Rosen EL. Bode JW. J. Am. Chem. Soc. 2004, 126: 14370

Google Scholar
138b Burstein C. Glorious F. Angew. Chem. Int. Ed. 2004, 43: 6205

Google Scholar
139 Li Y. Zhao Z.-A. He H. You S.-L. Adv. Synth. Catal. 2008, 350: 1885

Crossref Google Scholar
140a Bui T. Barbas CF. Tetrahedron Lett. 2000, 41: 6951

Google Scholar
140b Huang Y. Walji AM. Larsen CH. MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051

Google Scholar
140c Marigo M. Schulte T. Franzén J. Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 15710

Google Scholar
140d Yang JW. Hechavarria Fonseca MT. List B. J. Am. Chem. Soc. 2005, 127: 15036

Google Scholar
141a Enders D. Grondal C. Hüttl M. Angew. Chem. Int. Ed. 2007, 46: 1570

Google Scholar
141b Wang W. Yu X. Org. Biomol. Chem. 2008, 2037

Google Scholar
142 Zhao GL. Vesely J. Rios R. Ibrahem I. Sundén H. Córdova A. Adv. Synth. Catal. 2008, 350: 657

Crossref Google Scholar
143 Ibrahem I. Zhao GL. Rios R. Vesely J. Sundén H. Dziedzic P. Córdova A. Chem. Eur. J. 2008, 14: 7868

Google Scholar
144 Enders D. Wang C. Bats JW. Angew. Chem. Int. Ed. 2008, 47: 7539

Crossref PubMed Google Scholar
145a Tan B. Chua PJ. Li Y. Zhong G. Org. Lett. 2008, 10: 2437

Google Scholar
145b Tan B. Chua PJ. Zeng X. Lu M. Zhong G. Org. Lett. 2008, 10: 3489

Google Scholar
146 Tan B. Shi Z. Chua PJ. Zhong G. Org. Lett. 2008, 10: 3425

Crossref Google Scholar
147 Enders D. Hüttl MRM. Grondal C. Raabe G. Nature 2006, 441: 861

Google Scholar
148 Penon O. Carlone A. Mazzanti A. Locatelli M. Sambri L. Bartoli G. Melchiorre P. Chem. Eur. J. 2008, 14: 4788

Crossref PubMed Google Scholar
149 Bertelsen S. Johansen RL. Jørgensen KA. Chem. Commun. 2008, 3016

Crossref Google Scholar

1

Current address: Dipartimento di Ingegneria Meccanica e Industriale, Università degli Studi ‘Roma Tre’, 00146, Roma, Italy; e-mail: tgasperi@uniroma3.it.