Unique reactivity of α,β-unsaturated carboxylic acid imidazolides: Catalytic asymmetric synthesis of α,β-epoxy esters and α,β-epoxy carboxylic acid derivatives

Tetsuhiro Nemoto, Shin Ya Tosaki, Takashi Ohshima, Masakatsu Shibasaki

研究成果: ジャーナルへの寄稿学術誌査読

14 被引用数 (Scopus)

抄録

Catalytic asymmetric synthesis of α,β-epoxy esters and α,β-epoxy carboxylic acid derivatives is described. Catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides using La-BINOL-Ph3As=O complex gave the corresponding α,β-epoxy peroxy tert-butyl esters, which were directly converted to the α,β-epoxy methyl esters by adding methanol to the reaction. This catalytic system had broad generality for epoxidation of various substrates. With the use of 5-10 mol% of the catalyst, both β-aryl and β-alkyl-substituted-α,β-epoxy methyl esters were obtained in up to 91% yield and in up to 93% enantiomeric excess. In addition, efficient transformations of α,β-epoxy peroxy tert-butyl esters into the α,β-epoxy amides, α,β-epoxy aldehydes, and γ,δ-epoxy β-keto esters are also reported.

本文言語英語
ページ(範囲)306-311
ページ数6
ジャーナルChirality
15
4
DOI
出版ステータス出版済み - 2003
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 創薬
  • 分析化学
  • 分光学
  • 触媒
  • 薬理学
  • 有機化学

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