Formal Methylene Insertion into the C–H Bond of α-Carbonyl Aldonitrones with Dimethylsulfoxonium Methylide

  • Sakurai Takanobu
  • Yano Tohru
  • Suga Takuya
  • Soeta Takahiro
  • Ukaji Yutaka
  • 菅 拓也
  • 添田 貴宏
  • 宇梶 裕
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Publication date
October 2022
Publisher
The Chemical Society of Japan
Journal
Bulletin of the Chemical Society of Japan

Abstract

金沢大学理工学研究域物質化学系A methylene group was introduced into the C–H bond of α-carbonyl aldonitrones by reaction with dimethylsulfoxonium methylide, producing one-carbon homologated C-methyl ketonitrones. This formal methylene insertion was applied to one-pot synthesis of quaternary C3-methyl isoxazolidines via successive 1,3-dipolar cycloaddition with alkenes bearing an electron withdrawing group

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