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

Jonathan Clayden; Eric W. Collington; Stuart Warren

doi:10.1016/S0040-4039(00)60928-0

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

Jonathan Clayden^*, Eric W. Collington, Stuart Warren

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (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 language	English
Pages (from-to)	7043-7046
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(00)60928-0
Publication status	Published - 10 Nov 1992

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title = "Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides",

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.",

author = "Jonathan Clayden and Collington, {Eric W.} and Stuart Warren",

year = "1992",

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T1 - Asymmetric epoxidations and kinetic resolutions of δ-hydroxy allylic phosphine oxides

AU - Clayden, Jonathan

AU - Collington, Eric W.

AU - Warren, Stuart

PY - 1992/11/10

Y1 - 1992/11/10

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4039(00)60928-0

DO - 10.1016/S0040-4039(00)60928-0

M3 - Article (Academic Journal)

AN - SCOPUS:0026466869

VL - 33

SP - 7043

EP - 7046

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -