Issue 6, 1991
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reaction

Paul S. Brown,   Nicholas Greeves,   Andrew B. McElroy  and  Stuart Warren  

Abstract

Acylation of Ph2P(O) Me with a lactone gives a Horner–Wittig intermediate with a Z-double bond protected as a Diels–Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol. Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner–Wittig reaction. The geometry of only one double bond can be controlled.

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Article information

DOI
https://doi.org/10.1039/P19910001485
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 1485-1492

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The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reaction

P. S. Brown, N. Greeves, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 1485 DOI: 10.1039/P19910001485

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