Catalytic asymmetric Horner-Wadsworth-Emmons reaction under phase-transfer-catalyzed conditions

被引：81

作者：

Arai, S ^{[1
]}

Hamaguchi, S ^{[1
]}

Shioiri, T ^{[1
]}

机构：

[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期

关键词：

asymmetric reactions; catalysts; olefination; phase transfer;

D O I：

10.1016/S0040-4039(98)00442-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric Homer-Wadsworth-Emmons reaction promoted by quaternary ammonium salts derived from cinchonine as a phase-transfer catalyst is described. Treatment of the prochiral ketone 1 with phosphonates under mild reaction conditions afforded the corresponding desired products in moderate enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2997 / 3000

页数：4

共 14 条

[1] ASYMMETRIC CARBOALKOXYALKYLIDENATION WITH A CHIRAL HORNER-WADSWORTH-EMMONS REAGENT [J].

DENMARK, SE ;

RIVERA, I .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :6887-6889

[2] ELECTROPHILIC ACTIVATION OF THE HORNER-WADSWORTH-EMMONS-WITTIG REACTION - HIGHLY SELECTIVE SYNTHESIS OF DISSYMMETRIC OLEFINS [J].

DENMARK, SE ;

CHEN, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10674-10676

[3] STUDIES IN ASYMMETRIC OLEFINATIONS - THE SYNTHESIS OF ENANTIOMERICALLY PURE ALLYLIDENE, ALKYLIDENE, AND BENZYLIDENE CYCLOHEXANES [J].

HANESSIAN, S ;

BEAUDOIN, S .

TETRAHEDRON LETTERS, 1992, 33 (50) :7655-7658

[4] VERSATILE SYNTHESIS OF ALICYCLIC AND ACYCLIC COMPOUNDS WITH ALTERNATE AND REMOTE C-METHYL SUBSTITUTION PATTERNS VIA ASYMMETRIC SEQUENTIAL OLEFINATION AND ENE REACTIONS [J].

HANESSIAN, S ;

BEAUDOIN, S .

TETRAHEDRON LETTERS, 1992, 33 (50) :7659-7662

[5] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES [J].

KANN, N ;

REIN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3802-3804

[6] ASYMMETRIC SELENOXIDE ELIMINATION LEADING TO CHIRAL ALKYL AND ARYL CYCLOHEXYLIDENEMETHYL KETONES [J].

KOMATSU, N ;

MATSUNAGA, S ;

SUGITA, T ;

UEMURA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5847-5848

[7]

Kumamoto T, 1997, CHEM PHARM BULL, V45, P753

[8] ELECTRONIC CONTROL OF ENANTIOSELECTIVITY IN THE PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION OF TRANS 4-TBUTYL-1-VINYLCYCLOHEXYL BENZOATES [J].

LEGROS, JY ;

FIAUD, JC .

TETRAHEDRON, 1994, 50 (02) :465-474

[9]

MUSIEROWICZ S, 1975, TETRAHEDRON LETT, P437

[10] KINETIC RESOLUTION OF ALPHA-SUBSTITUTED KETONES BY WITTIG REACTION USING A CHIRAL TRICYCLIC PHOSPHONATE [J].

NARASAKA, K ;

HIDAI, E ;

HAYASHI, Y ;

GRAS, JL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :102-104

← 1 2 →