Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone

Chun Yu Ho, Ying Chun Chen, Man Kin Wong, Dan Yang

Research output: Journal article publicationJournal articleAcademic researchpeer-review

64 Citations (Scopus)

Abstract

(Chemical Equation Presented) We have synthesized a series of chiral cyclic secondary amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine plays a dual role - as a phase transfer catalyst and an Oxone activator - in these epoxidation reactions. The slightly acidic reaction conditions we employed in this work obviate the need to preform ammonium salts, which are the actual catalysts that mediate the epoxidations.
Original languageEnglish
Pages (from-to)898-906
Number of pages9
JournalJournal of Organic Chemistry
Volume70
Issue number3
DOIs
Publication statusPublished - 4 Feb 2005
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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