Copper-catalyzed skeletal rearrangement of o -propargylic aryloximes into four-membered cyclic nitrones - Chirality transfer and mechanistic insight

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

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)]in acetonitrile at 70C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

Original languageEnglish
Pages (from-to)1542-1550
Number of pages9
JournalSynthesis
Volume44
Issue number10
DOIs
Publication statusPublished - 2012 Apr 25

Keywords

  • chirality transfer
  • copper
  • nitrone
  • oxime
  • skeletal rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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