Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides

Jonathan Clayden*, Eric W. Collington, Stuart Warren

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

6 Citations (Scopus)

Abstract

δ-Hydroxy allylic phosphine-oxides 5 undergo asymmetric epoxidation to yield epoxy alcohols 6 with high enantio- and diastereoselectivity. Kinetic resolutions are also successful, even with a chiral centre remote from the allylic hydroxyl, if that chiral centre bears a diphenylphosphinoyl group. The diphenylphosphinoyl group then exerts a novel anti-directing effect on the epoxidation.

Original languageEnglish
Pages (from-to)7043-7046
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number46
DOIs
Publication statusPublished - 10 Nov 1992

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