Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides

Harufumi Oyama, Masahisa Nakada

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides with indole, pyrrole, and furan derivatives at relatively low temperatures are described. The X-ray crystallographic analysis of the product revealed that the sense of enantioselectivity of the Friedel-Crafts reactions could be well explained by the proposed chelate model. The model was stabilized by an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.

Original languageEnglish
Pages (from-to)195-202
Number of pages8
JournalTetrahedron Asymmetry
Volume26
Issue number4
DOIs
Publication statusPublished - 2015 Feb 28

ASJC Scopus subject areas

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

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