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

作者信息

Perrard T, Plaquevent J C, Desmurs J R, Hébrault D

机构信息

Laboratoire des Fonctions Azotées et Oxygénées Complexes - IRCOF, UPRES-A CNRS 6014, Faculté des Sciences, rue Tesnière, F-76821 Mont Saint Aignan Cedex, France.

出版信息

Org Lett. 2000 Sep 21;2(19):2959-62. doi: 10.1021/ol006207e.

DOI:10.1021/ol006207e

PMID:10986082

Abstract

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.

摘要