The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition

Jonathan Clayden; Stuart Warren

The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition

Jonathan Clayden, Stuart Warren^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

9 Citations (Scopus)

Abstract

Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph₂PO) group, is regiospecific (acetate moves away from the Ph₂PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.

Original language	English
Pages (from-to)	2913-2923
Number of pages	11
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	23
Publication status	Published - 1 Dec 1993

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Organic & Biological

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title = "The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition",

abstract = "Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph2PO) group, is regiospecific (acetate moves away from the Ph2PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.",

author = "Jonathan Clayden and Stuart Warren",

year = "1993",

month = dec,

day = "1",

language = "English",

pages = "2913--2923",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "23",

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TY - JOUR

T1 - The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition

AU - Clayden, Jonathan

AU - Warren, Stuart

PY - 1993/12/1

Y1 - 1993/12/1

N2 - Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph2PO) group, is regiospecific (acetate moves away from the Ph2PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.

AB - Palladium(II)-catalysed allylic acetate transposition, when driven by the diphenylphosphinoyl (Ph2PO) group, is regiospecific (acetate moves away from the Ph2PO group), stereoselective (the new double bond is E), and stereospecific (the acetate moves suprafacially across the allyl system). The rearranged acetates can be hydrolysed to δ-hydroxy allylic phosphine oxides which are useful intermediates in a variety of synthetic methods.

UR - https://www.scopus.com/pages/publications/37049086674

M3 - Article (Academic Journal)

AN - SCOPUS:37049086674

SN - 0300-922X

SP - 2913

EP - 2923

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 23

ER -

The synthesis of δ-hydroxy allylic phosphine oxides by palladium(II)-catalysed allylic acetate transposition

Abstract

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