Asymmetric epoxidation of α,β-unsaturated ketones with hydrogen peroxide catalyzed by axially chiral guanidine base

Masahiro Terada, Megumi Nakano

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

The enantioselective epoxidation of α,β-unsaturated ketones with hydrogen peroxide was demonstrated using axially chiral guanidine as a base catalyst. Hydrogen peroxide can be utilized as a cost-effective and atom-efficient oxidant in the present catalytic epoxidation even under heterogeneous conditions. The newly developed axially chiral guanidine base bearing an additional central chirality functions as an efficient catalyst to provide epoxides in 51-65% ee.

Original languageEnglish
Pages (from-to)1049-1055
Number of pages7
JournalHeterocycles
Volume76
Issue number2
DOIs
Publication statusPublished - 2008 Nov 1

Keywords

  • Asymmetric Catalyst
  • Brønsted Base
  • Enantioselectivity
  • Organocatalyst

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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