The enantioselective morita-baylis-hiliman reaction and its aza counterpart

被引:488
作者
Masson, Geraldine [1 ]
Housseman, Christopher [1 ]
Zhu, Jieping [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
asymmetric synthesis; Bronsted acids; Lewis bases; organocatalysis; reaction mechanisms;
D O I
10.1002/anie.200604366
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of asymmetric Morita-Baylis-Hillman (MBH) reactions has evolved dramatically over the past few years, parallel to the emerging concept of bifunctional organocatalysis. Whereas organocatalysis is starting to compete with metal-based catalysis in several important organic transformations, the MBH reaction belongs to a group of prototypical reactions in which organocatalysis already display superiority over their metal-based counterparts. This Minireview summarizes recent mechanistic insights and advances in the design and synthesis of small organic molecules for enantioselective MBH and aza-MBH reactions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4614 / 4628
页数:15
相关论文
共 182 条
[31]   Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts [J].
Berkessel, Albrecht ;
Roland, Katrin ;
Neudoerfl, Jorg M. .
ORGANIC LETTERS, 2006, 8 (19) :4195-4198
[32]   Modified BINAP: The how and the why [J].
Berthod, M ;
Mignani, G ;
Woodward, G ;
Lemaire, M .
CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836
[33]   Conformation-directed macrocyclization reactions [J].
Blankenstein, J ;
Zhu, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (10) :1949-1964
[34]   A KINETIC AND MECHANISTIC STUDY OF THE BAYLIS-HILLMAN REACTION [J].
BODE, ML ;
KAYE, PT .
TETRAHEDRON LETTERS, 1991, 32 (40) :5611-5614
[35]   BINOL: A versatile chiral reagent [J].
Brunel, JM .
CHEMICAL REVIEWS, 2005, 105 (03) :857-897
[36]   The asymmetric Baylis-Hillman reaction [J].
Brzezinski, LJ ;
Rafel, S ;
Leahy, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318
[37]   Bifunctional activation and racemization in the catalytic asymmetric aza-Baylis-Hillman reaction [J].
Buskens, P ;
Klankermayer, J ;
Leitner, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16762-16763
[38]   Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water [J].
Cai, JX ;
Zhou, ZH ;
Zhao, GF ;
Tang, CC .
ORGANIC LETTERS, 2002, 4 (26) :4723-4725
[39]   Asymmetric Baylis-Hillman reactions using (R)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid acrylate derivatives in solution and on solid support [J].
Calmès, M ;
Akkari, R ;
Barthes, N ;
Escale, F ;
Martinez, J .
TETRAHEDRON-ASYMMETRY, 2005, 16 (12) :2179-2185
[40]   An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis-Hillman reaction [J].
Chen, SH ;
Hong, BC ;
Su, CF ;
Sarshar, S .
TETRAHEDRON LETTERS, 2005, 46 (51) :8899-8903