Skeletal rearrangement of O-propargylic formaldoximes by a gold-catalyzed cyclization/intermolecular methylene transfer sequence

Itaru Nakamura, Shinya Gima, Yu Kudo, Masahiro Terada

研究成果: Article査読

27 被引用数 (Scopus)

抄録

Abstract Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts, afforded 4-methylene-2-isoxazolines in good to excellent yields by an intermolecular methylene transfer. In addition, the cascade reaction with maleimide in the presence of a gold catalyst afforded isoxazole derivatives by cyclization/methylene transfer and a subsequent ene reaction, whereas that using a copper catalyst gave oxazepines through a 2,3-rearrangement. Au is not like Cu: Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts effectively afforded 4-methylene-2-isoxazolines by intermolecular methylene transfer. The cascade reaction in the presence of gold proceeds by cyclization/methylene transfer and a subsequent ene reaction, whereas with a copper catalyst it proceeds by a 2,3-rearrangement.

本文言語English
ページ(範囲)7154-7157
ページ数4
ジャーナルAngewandte Chemie - International Edition
54
24
DOI
出版ステータスPublished - 2015 6 1

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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