Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis

被引：82

作者：

Perrard, T

Plaquevent, JC

Desmurs, JR

Hébrault, D

机构：

[1] Fac Sci, UPRES A CNRS 6014, IRCOF, Lab Fonct Azotees & Oxygenees Complexes, F-76821 Mt St Aignan, France

[2] Ctr Rech Lyon, F-69192 St Fons, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 19期

关键词：

D O I：

10.1021/ol006207e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Both enantiomers of methyl dihydrojasmonate (-)-1 and (+)-1 were obtained by a short route using asymmetric Michael addition of dimethyl malonate onto pentyl enone 3, followed by nonracemizing demethoxycarbonylation. The key enantioselective step involves a new system of asymmetric solid-liquid phase-transfer catalysis using solvent-free conditions, Enantiomeric excess as high as 90% (91% yield) was achieved.

引用

页码：2959 / 2962

页数：4

共 34 条

[1]

[Anonymous], [No title captured], Patent No. [US 5874600 A, 5874600]

[2]

COLONNA S, 1980, AFINIDAD, V38, P501

[3] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst [J].