Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes

Wing Kei Chan, Man Kin Wong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

21 Citations (Scopus)

Abstract

By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H 2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals.
Original languageEnglish
Pages (from-to)4226-4232
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number11
DOIs
Publication statusPublished - 27 May 2005
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this