Regioselective transformation of O-propargylic arylaldoximes to four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement

Itaru Nakamura, Toshiharu Araki, Dong Zhang, Yu Kudo, Eunsang Kwon, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

(E)-O-Propargylic arylaldoximes were regioselectively converted, in the presence of copper catalysts, into their corresponding four-membered cyclic nitrones in good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4π-electrocyclization of the N-allenylnitrone intermediate and involved cleavage of the carbon-oxygen bond.

Original languageEnglish
Pages (from-to)3616-3619
Number of pages4
JournalOrganic letters
Volume13
Issue number14
DOIs
Publication statusPublished - 2011 Jul 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Regioselective transformation of O-propargylic arylaldoximes to four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement'. Together they form a unique fingerprint.

Cite this