In the golden age of organocatalysis

Angewandte Chemie - International Edition

Volumn 43, Issue 39, 2004, Pages 5138-5175

  Dalko, Peter I ^a,c,d,e,f,g   Moisan, Lionel ^b,g,h,i  

^a CNRS   (France)

^b CEA SACLAY   (France)

^c BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^d Texas A and M University ^*

^e TEXAS A AND M UNIVERSITY   (United States)

^f HARVARD UNIVERSITY   (United States)

^g PSL RESEARCH UNIVERSITY   (France)

^h SORBONNE UNIVERSITÉ   (France)

ⁱ DIF   (France)

Author keywords

Asymmetric catalysis; Chiral auxiliaries; Organocatalysis; Synthetic methods

Indexed keywords

GOLDEN AGE; MOLECULAR SKELETONS; ORGANOCATALYSIS;

ACCELERATION; CATALYST SELECTIVITY; ORGANIC COMPOUNDS; REACTION KINETICS; STOICHIOMETRY;

ORGANOMETALLICS;

ORGANIC COMPOUND;

ALDOL REACTION; ALKYLATION; AMINATION; BAEYER VILLIGER REACTION; CATALYSIS; CYCLOADDITION; CYCLOPROPANATION; EPOXIDATION; MANNICH REACTION; OXIDATION; PHASE TRANSITION; PHOSPHORYLATION; PROTON TRANSPORT; REVIEW; STRECKER SYNTHESIS; SYNTHESIS;

EID: 6044269452     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200400650     Document Type: Review

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121. A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 7749-7752.
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127. B. List, C. Castello, Synlett 2001, 1687-1689.
128. P. Pojarliev, W. T. Biller, H. J. Martin, B. List, Synlett 2003, 1903-1905.
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136. see also: d) H. Iwamura, S. P. Mathew, D. G. Blackmond, J. Am. Chem. Soc. 2004, 726, ASAP, DOI: 10.1021/ja046258x: for a Review, see: e) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058; Angew. Chem. Int. Ed. 2004, 45, 2995-2997.
137. see also: d) H. Iwamura, S. P. Mathew, D. G. Blackmond, J. Am. Chem. Soc. 2004, 726, ASAP, DOI: 10.1021/ja046258x: for a Review, see: e) P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058; Angew. Chem. Int. Ed. 2004, 45, 2995-2997.
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151. For reviews, see: a) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196; c) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061.
152. For reviews, see: a) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894; b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196; c) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061.
153. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
154. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
155. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
156. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
157. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
158. For related metal-complex-catalyzed asymmetric conjugate additions, see, for example: a) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; b) T. Hayashi, Synlett 2001, 879-887; c) A. Duursma, A. J. Minnaard, B. L. Feringa, Tetrahedron 2002, 58, 5773-5778; d) A. Alexakis, C. Benhaim, S. Rosset, M. Humam, J. Am. Chem. Soc. 2002, 124, 5262-5263; e) A. Rimkus, N. Sewald, Org. Lett. 2003, 5, 79-80; f) D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105.
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162. d) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267;
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164. for intramolecular addition, see: e) M. T. Hechavarria Fronseca, B. List, Angew. Chem. 2004, 116, 4048-4050; Angew. Chem. Int. Ed. 2004, 43, 3958-3960.
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489. For recent reviews, see: a) C. Alexander, L. Davidson, W. Hayes, Tetrahedron 2003, 59, 2025-2056; b) G. Wulff, Chem. Rev. 2002, 102, 1-28; c) W. B. Motherwell, M. J. Bingham, Tetrahedron 2001, 57, 4663-4686; d) B. Clapham, T. S. Reger, K. D. Janda, Tetrahedron 2001, 57, 4637-4662.
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503. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
504. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
505. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
506. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
507. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
508. For some recent examples, see: a) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035-6037; Angew. Chem. Int. Ed. 2003, 42, 5855-5857; b) A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2003, 125, 1612-1613; c) W. Zhou, L. Liu, R. Breslow, Helv. Chim. Acta 2003, 86, 3560-3567; d) H. Kuroda, I. Tomita, T. Endo, Org. Lett. 2003, 5, 129-131; e) C. A. Evans, S. J. Miller, J. Am. Chem. Soc. 2003, 125, 12 394-12 395; f) X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716-4717.
509. For the dynamic kinetic resolution of Morita-Baylis-Hillman acetates, see: C.-W. Cho, J.-R. Kong, M. J. Krische, Org. Lett. 2004, 6, 1337-1339.
510. For halogenation, see: a) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108-4109; b) M. Marigo, N. Kumaragurubaran, K. A. Jørgensen, Eur. J. Org. Chem. 2004, 2133-2137; c) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790-4791.
511. For halogenation, see: a) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108-4109; b) M. Marigo, N. Kumaragurubaran, K. A. Jørgensen, Eur. J. Org. Chem. 2004, 2133-2137; c) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790-4791.
512. For halogenation, see: a) M. P. Brochu, S. P. Brown, D. W. C. MacMillan, J. Am. Chem. Soc. 2004, 126, 4108-4109; b) M. Marigo, N. Kumaragurubaran, K. A. Jørgensen, Eur. J. Org. Chem. 2004, 2133-2137; c) N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790-4791.
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