Catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and amides by lanthanide-BINOL complexes

Takashi Ohshima, Tetsuhiro Nemoto, Shin Ya Tosaki, Hiroyuki Kakei, Vijay Gnanadesikan, Masakatsu Shibasaki

研究成果: Contribution to journalArticle査読

33 被引用数 (Scopus)

抄録

Highly enantioselective catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and simple amides was developed. In the presence of 5-10mol% of lanthanide-BINOL complexes, the reaction proceeded smoothly with high substrate generality. In particular, in the cases of α,β-unsaturated amides, there was nearly perfect enantioselectivity (>99% ee). The corresponding epoxides were successfully transformed into many types of useful chiral compounds such as α,β-epoxy esters, α,β-epoxy amides, α,β-epoxy aldehydes, α,β-epoxy β-keto ester, and α- and β-hydroxy carbonyl compounds. B3LYP density functional studies were performed to predict substrate reactivity.

本文言語英語
ページ(範囲)10485-10497
ページ数13
ジャーナルTetrahedron
59
52
DOI
出版ステータス出版済み - 12 22 2003
外部発表はい

All Science Journal Classification (ASJC) codes

  • 生化学
  • 創薬
  • 有機化学

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