A NEW ENANTIOSELECTIVE SYNTHESIS OF GLYCIDATES VIA DYNAMIC KINETIC RESOLUTION OF RACEMIC 2-CHLORO-3-KETO ESTERS USING CHIRAL RU(II) COMPLEXES

被引：68
|
作者：
GENET, JP
DEANDRADE, MCC
RATOVELOMANANAVIDAL, V
机构：
[1] Laboratoire de Synthèse Organique, Associé au C.N.R.S., Ecole Nationale Supérieure de Chimie de Paris, 75231 Paris Cedex 05
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 12期
关键词：
ASYMMETRIC HYDROGENATION; CHIRAL RUTHENIUM (II) CATALYSTS; DYNAMIC KINETIC RESOLUTION; 2,3-EPOXY ESTERS;
D O I：
10.1016/0040-4039(95)00182-C
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (Ii) catalysts prepared in-situ from (COD)Ru(2-Methylallyl)(2) in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%. 2-chloro-3-hydroxy esters were treated with different bases to give (E)- and (Z)-2,3-epoxyalkanoates in 65-90% yields with 84-97% ee.
引用
收藏
页码：2063 / 2066
页数：4
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