The first example of an amide-carbonyl stabilized oxiranyl anion: Generation from epoxysilane, its properties, and trapping with electrophiles

Tsuyoshi Satoh, Takayuki Shimura, Ken Sakai

研究成果: Contribution to journalArticle査読

9 被引用数 (Scopus)

抄録

An epoxysilane having an amide group at the a-carbon was synthesized from phenylacetylene. An amide-carbonyl stabilized oxiranylammonium was generated from the epoxysilane in THF with tetrabutylammonium fluoride (TBAF). The generated oxiranyl anion was found to have enough nucleophilicity with aldehydes to give moderate to good yields of the adducts. In some reactions, the oxiranylammonium was found to be configurationally unstable to give the epimers.

本文言語英語
ページ(範囲)137-147
ページ数11
ジャーナルHeterocycles
59
1
DOI
出版ステータス出版済み - 1 1 2003
外部発表はい

All Science Journal Classification (ASJC) codes

  • 分析化学
  • 薬理学
  • 有機化学

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