Diastereoselective epoxidation of cyclohexene derivatives by dioxiranes generated in situ. Importance of steric and field effects

Dan Yang, Guan Sheng Jiao, Yiu Chung Yip, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

49 Citations (Scopus)

Abstract

In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.
Original languageEnglish
Pages (from-to)1635-1639
Number of pages5
JournalJournal of Organic Chemistry
Volume64
Issue number5
DOIs
Publication statusPublished - 5 Mar 1999
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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