The Journal of organic chemistry

A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives

R Imashiro, M Seki

Index: Imashiro, Ritsuo; Seki, Masahiko Journal of Organic Chemistry, 2004 , vol. 69, # 12 p. 4216 - 4226

Full Text: HTML

Citation Number: 71

Abstract

A novel and practical asymmetric synthesis of chiral glycidic acid derivatives involving methyl (2 R, 3 S)-3-(4-methoxyphenyl) glycidate ((2 R, 3 S)-2a), a key intermediate for diltiazem hydrochloride (1), was developed. Treatment of methyl (E)-4-methoxycinnamate ((E)-3a) with chiral dioxirane, generated in situ from a catalytic amount (5 mol%) of an 11- membered C 2-symmetric binaphthyl ketone (R)-7a, provided (2 R, 3 S)-2a in 92% yield ...