Amine-catalyzed direct self Diels-Alder reactions of α,β-unsaturated ketones in water:: synthesis of pro-chiral cyclohexanones

被引：104

作者：

Ramachary, DB

Chowdari, NS

Barbas, CF

机构：

[1] Scripps Res Inst, Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 38期

基金：

美国国家卫生研究院;

关键词：

amines; cyclohexanones; Diels-Alder reactions; organocatalysis; enamines; imines; aqueous media;

D O I：

10.1016/S0040-4039(02)01500-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amine-catalyzed direct self Diels-Alder reactions of alpha, beta-unsaturated ketones have been developed. (S)-1-(2-Pyrrolidinyl-methyl)pyrrolidine, L-proline and pyrrolidine catalyzed the reaction of alpha,beta-unsaturated ketones to provide cyclohexanone derivatives with good yield (up to 80%) in a single step via in situ-generation of 2-amino-1,3-butadienes and iminium ion-activated enones. Pro-chiral cyclohexanones were selectively prepared with pyrrolidine catalysis in water. (C) 2002 Published by Elsevier Science Ltd.

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页码：6743 / 6746

页数：4

相关论文

共 24 条

[1] THE PROLINE AND BETA-LACTOGLOBULIN MEDIATED ASYMMETRIC SELF-CONDENSATION OF BETA-IONYLIDENEACETALDEHYDE, RETINAL AND RELATED-COMPOUNDS [J].

ASATO, AE ;

WATANABE, C ;

LI, XY ;

LIU, RSH .

TETRAHEDRON LETTERS, 1992, 33 (22) :3105-3108

[2] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[3] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

[4] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

[5] A proline-catalyzed asymmetric Robinson annulation reaction [J].

Bui, T ;

Barbas, CF .

TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954

[6] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[7] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[8] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

[9]

Evans D. A., 1999, COMPREHENSIVE ASYMME, V3, P1177

[10] Special reactions of α,β-unsaturated ketones III.: Formation and structure elucidation of dimers of 2-arylmethyleneketones:: (5E)-5-benzylidene-9β-phenyl-trans-4a-1,2,3,4,4a,5,6,7,8,9a-decahydroxanthen-4aα-ol and 3β,5β-bis-(4-methoxyphenyl)-2α,4β,6α-trimethyl-4α-propionyl-cyclohexanone [J].

Gössnitzer, E ;

Wendelin, W ;

Schermanz, K ;

Frieberger, K .

MONATSHEFTE FUR CHEMIE, 2001, 132 (09) :1081-1093