The conjugate addition of a silyl group to enones and its removal with copper(II) bromide: a protecting group for the αβ-unsaturation of αβ-unsaturated ketones
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2520-2526
- https://doi.org/10.1039/p19810002520
Abstract
Silyl-lithium reagents mixed with copper(I) salts react with enones, including esters and aldehydes, to give β-silyl carbonyl compounds in good yield. The β-silylketones can be used in synthesis without risk to the silyl group and the enone group can be restored by bromination-desilylbromination with copper(II) bromide. The principle is illustrated with syntheses of carvone and dihydrojasmone.Keywords
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