Nucleophilic attack on a carbonyl group conjugated to a chiral centre: a search for a vinylogous Cram's rule
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 725-728
- https://doi.org/10.1039/p19860000725
Abstract
In a search for a vinylogous version of Cram's rule, 1,4-diphenylbut-2-ene-1,4-dione (5), 4-methoxy-1,4-diphenylbut-2-en-1-one (9), and hex-3-ene-2,5-dione (13) are found to be reduced with low or negligible diastereoselectivity. Similarly, the phenyl Grignard reagent showed no diastereoselectivity in its reaction with 4-methoxy-4-phenylbut-2-enal (12)Keywords
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