Unsaturated carboxylic acid polyenolates. Lithium trienolate of sorbic acid as a d6synthon: addition to ketones and unsaturated ketones
- 1 January 1988
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2797-2803
- https://doi.org/10.1039/p19880002797
Abstract
Deprotonation of sorbic acid by two equivalents of lithium diethylamide, and aldol-type reaction of the resulting trienolate dianion (2) with carbonylic compounds affords the pentadienyl hydroxy acids (6) or 7-hydroxyhexa-2,4-dienoic acids (7) according to the duration and temperature of the reaction. The reaction of the dianion (2) with α,β-unsaturated ketones gives 1,4-ε-adducts for di- or tri-substituted enones, but either 1,4-γ- or 1,4-α-adducts for monosubstituted enones.Keywords
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