Kinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones

D. Yang, G. S. Jiao, Y. C. Yip, T. H. Lai, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

30 Citations (Scopus)

Abstract

Kinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl3, tert-butyl, or CF3group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.
Original languageEnglish
Pages (from-to)4619-4624
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number13
DOIs
Publication statusPublished - 29 Jun 2001
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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