Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; Application to the synthesis of CDP-840

被引：96

作者：

Aggarwal, VK

Bae, I

Lee, HY

Richardson, J

Williams, DT

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea

[3] Korea Adv Inst Sci & Technol, Sch Mol Sci BK21, Taejon 305701, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 28期

关键词：

asymmetric synthesis; epoxidation; sulfur; synthetic methods; ylides;

D O I：

10.1002/anie.200350968

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Benzyl and substituted allyl sulfonium salts react with a broad range of simple and functionalized aldehydes and ketones to give epoxides with high diastereoselectivity and high enantioselectivity (see scheme). The process has been applied to a short synthesis of the phosphodiesterase-IV inhibitor CDP-840. R1, R2 = hydrogen, alkyl, alkenyl, alkynyl, aryl, or pyridyl.

引用

页码：3274 / 3278

页数：5

共 26 条

[1]

AGGARWAL VK, 2003, IN PRESS CHEM COMMUN

[2] CDP840. A prototype of a novel class of orally active anti-inflammatory phosphodiesterase 4 inhibitors [J].