Synthesis of (Z)-homoallylic alcohols and homoprop-2-ynylic alcohols via palladium-catalysed hydrogenolysis of prop-2-ynylic cyclic carbonates
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 237-238
- https://doi.org/10.1039/p19940000237
Abstract
The decarboxylation–hydrogenolysis of prop-2-ynylic cyclic carbonates which have an internal acetylenic bond with ammonium formate in the presence of a catalytic amount of [Pd(acac)2] and Bun 3P afforded (Z)-homoallylic alcohols or homoprop-2-ynylic alcohols depending on the reaction conditions, however, hydrogenolysis of terminal prop-2-ynylic cyclic carbonates gave homoallylic alcohols; using (Z)-homoallylic alcohol 2b as a chiral synthon, the male sex pheromone of the pyralid moth Aphomia gularis has been synthesized.Keywords
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