The opposite diastereoselectivity in the alkylation and protonation of enolates
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 904-905
- https://doi.org/10.1039/c39840000904
Abstract
The conjugate addition of BuCu·BF3 to the enoate (5) produces predominantly the syn-isomer (7) having the butyl and methyl groups syn on the carbon chain, while the methylation of the enolate derived from the ester (8) gives preferentially the other diastereoisomer, anti-(6); the diastereoselectivity can be explained by an eclipsed model.Keywords
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