The chiral diamine mediated asymmetric Baylis-Hillman reaction

被引：46

作者：

Hayashi, Y ^{[1
]}

Tamura, T ^{[1
]}

Shoji, M ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 9-10期

关键词：

asymmetric synthesis; Baylis-Hillman reaction; diamines; enones; Lewis base catalysts; organic catalysis;

D O I：

10.1002/adsc.200404069

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A chiral diamine, easily prepared from proline, is an effective, asymmetric organic catalyst for the Baylis-Hillman reaction of aldehydes and methyl vinyl ketone, affording adducts with enantio-selectivities up to 75%.

引用

页码：1106 / 1110

页数：5

共 39 条

[1] Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis-Hillman reaction [J].

Balan, D ;

Adolfsson, H .

TETRAHEDRON LETTERS, 2003, 44 (12) :2521-2524

[2] Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].

Barrett, AGM ;

Cook, AS ;

Kamimura, A .

CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534

[3] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[4] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[5]

Ciganek E., 1997, ORG REACTIONS, V51, P201

[6] An enantioselective Baylis-Hillman reaction catalyzed by chiral phosphines under atmospheric pressure [J].

Hayase, T ;

Shibata, T ;

Soai, K ;

Wakatsuki, Y .

CHEMICAL COMMUNICATIONS, 1998, (12) :1271-1272

[7] Direct proline-catalyzed asymmetric α-aminoxylation of ketones [J].

Hayashi, Y ;

Yamaguchi, J ;

Sumiya, T ;

Shoji, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1112-1115

[8] The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes [J].

Hayashi, Y ;

Tsuboi, W ;

Ashimine, I ;

Urushima, T ;

Shoji, M ;

Sakai, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3677-3680

[9] Application of high pressure induced by water-freezing to the direct catalytic asymmetric three-component List- Barbas-Mannich reaction [J].

Hayashi, Y ;

Tsuboi, W ;

Shoji, M ;

Suzuki, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11208-11209

[10] Direct proline catalyzed asymmetric α-aminooxylation of aldehydes [J].

Hayashi, Y ;

Yamaguchi, J ;

Hibino, K ;

Shoji, M .

TETRAHEDRON LETTERS, 2003, 44 (45) :8293-8296

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