Recent developments in the asymmetric organocatalytic Morita-Baylis-Hillman reaction

被引:98
作者
Pellissier, Helene [1 ]
机构
[1] Aix Marseille Univ, CNRS, Cent Marseille, iSm2, Marseille, France
关键词
Asymmetric (aza)-Morita-Baylis-Hillman reaction; Organocatalysis; Asymmetric catalysis; Chiral substrates; Allylic substitution reactions; 1,3-Dipolar cycloadditions; N-SULFONATED IMINES; METHYL VINYL KETONE; ALLYLIC-ALLYLIC ALKYLATION; CATALYZED 3+2 ANNULATION; ACTIVATED DOUBLE-BONDS; CHIRAL-PHOSPHINE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HILIMAN REACTION; BIFUNCTIONAL ORGANOCATALYSTS;
D O I
10.1016/j.tet.2017.04.008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The goal of this review is to collect the recent developments in asymmetric organocatalytic (aza)-Morita-Baylis-Hillman reactions reported since the beginning of 2013. It also includes the asymmetric organocatalysed transformations of racemic (aza)-Morita-Baylis-Hillman adducts, illustrating that they constitute synthetically important synthons in organic chemistry. It is divided into four sections, dealing successively with organocatalytic enantioselective Morita-Baylis-Hillman reactions, organocatalytic enantioselective aza-Morita-Baylis-Hillman reactions, asymmetric (aza)-Morita-Baylis-Hillman reactions of chiral substrates and asymmetric organocatalysed applications of Morita-Baylis-Hillman adducts. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2831 / 2861
页数:31
相关论文
共 164 条
[1]   Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].
Aggarwal, VK ;
Fulford, SY ;
Lloyd-Jones, GC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708
[2]  
[Anonymous], 2009, SYNTHESIS
[3]  
[Anonymous], 2010, RECENT DEV ASYMMETRI
[4]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[5]   A SIMPLE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXYALKANONES [J].
BASAVAIAH, D ;
GOWRISWARI, VVL .
TETRAHEDRON LETTERS, 1986, 27 (18) :2031-2032
[6]   Applications of Baylis-Hillman chemistry: enantioselective synthesis of (-)-methyl 3-aryl-2-methylene-3-(prop-2-yn-1-yloxy)propanoates via chiral leaving group strategy [J].
Basavaiah, D ;
Kumaragurubaran, N ;
Sharada, DS ;
Reddy, RM .
TETRAHEDRON, 2001, 57 (38) :8167-8172
[7]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[8]   The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].
Basavaiah, Deevi ;
Rao, Kalapala Venkateswara ;
Reddy, Raju Jannapu .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588
[9]   The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].
Basavaiah, Deevi ;
Veeraraghavaiah, Gorre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78
[10]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674