Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres

Jonathan Clayden; Stuart Warren

Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres

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

Saturated and unsaturated β- and δ-hydroxyalkyldiphenylphosphine oxides give adducts with aldehydes after treatment with an excess of butyllithium. Normal Horner-Wittig reactions lead to O-trityl (E,E)- and (E,Z)-hepta-2,4-dien-1-ols. Allylic rearrangement of the corresponding acetates catalysed by Pd^II can be used to control remote (1,4 or 1,7) relative stereochemistry across E alkenes.

Original language	English
Pages (from-to)	1529-1539
Number of pages	11
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	11
Publication status	Published - 1 Dec 1994

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Clayden, J., & Warren, S. (1994). Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres. Journal of the Chemical Society, Perkin Transactions 1, (11), 1529-1539.

Clayden, Jonathan ; Warren, Stuart. / Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides : Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres. In: Journal of the Chemical Society, Perkin Transactions 1. 1994 ; No. 11. pp. 1529-1539.

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title = "Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres",

abstract = "Saturated and unsaturated β- and δ-hydroxyalkyldiphenylphosphine oxides give adducts with aldehydes after treatment with an excess of butyllithium. Normal Horner-Wittig reactions lead to O-trityl (E,E)- and (E,Z)-hepta-2,4-dien-1-ols. Allylic rearrangement of the corresponding acetates catalysed by PdII can be used to control remote (1,4 or 1,7) relative stereochemistry across E alkenes.",

author = "Jonathan Clayden and Stuart Warren",

year = "1994",

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day = "1",

language = "English",

pages = "1529--1539",

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

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Clayden, J & Warren, S 1994, 'Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres', Journal of the Chemical Society, Perkin Transactions 1, no. 11, pp. 1529-1539.

Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres. / Clayden, Jonathan; Warren, Stuart.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 11, 01.12.1994, p. 1529-1539.

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

TY - JOUR

T1 - Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides

T2 - Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres

AU - Clayden, Jonathan

AU - Warren, Stuart

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Saturated and unsaturated β- and δ-hydroxyalkyldiphenylphosphine oxides give adducts with aldehydes after treatment with an excess of butyllithium. Normal Horner-Wittig reactions lead to O-trityl (E,E)- and (E,Z)-hepta-2,4-dien-1-ols. Allylic rearrangement of the corresponding acetates catalysed by PdII can be used to control remote (1,4 or 1,7) relative stereochemistry across E alkenes.

AB - Saturated and unsaturated β- and δ-hydroxyalkyldiphenylphosphine oxides give adducts with aldehydes after treatment with an excess of butyllithium. Normal Horner-Wittig reactions lead to O-trityl (E,E)- and (E,Z)-hepta-2,4-dien-1-ols. Allylic rearrangement of the corresponding acetates catalysed by PdII can be used to control remote (1,4 or 1,7) relative stereochemistry across E alkenes.

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M3 - Article (Academic Journal)

AN - SCOPUS:37049085918

SN - 0300-922X

SP - 1529

EP - 1539

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 11

ER -

Clayden J, Warren S. Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: Synthesis of O-protected (E,E)- and (E,Z)-hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres. Journal of the Chemical Society, Perkin Transactions 1. 1994 Dec 1;(11):1529-1539.

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