Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated anilides as ester surrogates

Zhihua Chen, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated carboxylic acid derivatives was achieved using anilide as a template. The Pr(Oi-Pr)3-6,6́-Ph-BINOL complex (10 mol%) with a Ph3P(O) (30 mol%) additive promoted the epoxidation of anilides in up to 99% yield and 88% ee. For α-methyl-β-Ph α,β- unsaturated anilide, the Gd(Oi-Pr)3-6,6′-I-BINOL complex (10 mol%) with Ar3P(O) (30 mol%, Ar = 4-methoxyphenyl) was suitable, giving epoxide in 87% yield and 78% ee.

Original languageEnglish
Pages (from-to)3529-3532
Number of pages4
JournalSynlett
Issue number20
DOIs
Publication statusPublished - Dec 18 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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