The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reaction
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1485-1492
- https://doi.org/10.1039/p19910001485
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.Keywords
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