Stereoselective synthesis of diltiazem via dynamic kinetic resolution

被引：40

作者：

Mordant, C ^{[1
]}

de Andrade, CC ^{[1
]}

Touati, R ^{[1
]}

Ratovelomanana-Vidal, V ^{[1
]}

Hassine, BB ^{[1
]}

Genet, JP ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, UMR 7573 CNRS, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France

来源：

SYNTHESIS-STUTTGART | 2003年 / 15期

关键词：

diltiazem; drugs; kinetic resolution; asymmetric catalysis; hydrogenations; ruthenium;

D O I：

10.1055/s-2003-42397

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of diltiazem has been developed using dynamic kinetic resolution (DKR) as a key step. The methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate was synthesized from a racemic mixture of alpha-chloro-beta-keto ester, with high anti diastereoselectivity (92%) and enantioselectivity (95%), based on an asymmetric hydrogenation reaction with a chiral ruthenium(II) catalyst, simply prepared by mixing Ru(cod)(2-methylallyl)(2) with the atropisomeric ligand (S)-MeO-BIPHEP. By treatment of this alpha-chloro-beta-hydroxy ester with a base, the corresponding trans methyl glycidate, a key intermediate of diltiazem, was easily obtained.

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页码：2405 / 2409

页数：5

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