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) › peer-review

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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",

month = nov,

day = "10",

doi = "10.1016/S0040-4039(00)60928-0",

language = "English",

volume = "33",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "46",

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TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0026466869&partnerID=8YFLogxK

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

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

M3 - Article (Academic Journal)

AN - SCOPUS:0026466869

SN - 0040-4039

VL - 33

SP - 7043

EP - 7046

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

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

Abstract

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