Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides

Kazuaki Enomoto, Harufumi Oyama, Masahisa Nakada

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides are described. The high reactivity of the cyclic α-alkylidene β-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with CuII through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.

Original languageEnglish
Pages (from-to)2798-2802
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number7
DOIs
Publication statusPublished - 2015 Feb 9

Keywords

  • Asymmetric catalysis
  • Cycloadditions
  • Enantioselectivity
  • Imides
  • Ynamides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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