Highly enantioselective catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides

Harufumi Oyama, Kohei Orimoto, Takashi Niwa, Masahisa Nakada

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Abstract Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.

Original languageEnglish
Article number59259
Pages (from-to)262-270
Number of pages9
JournalTetrahedron Asymmetry
Volume26
Issue number5-6
DOIs
Publication statusPublished - 2015 Mar 28

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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