Chiral α-Substituted Carbonyls and Alcohols from the SN2‘ Displacement of Cuprates on Chiral Carbonates: An Alternative to the Alkylation of Chiral Enolates
- 13 September 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (21) , 7091-7097
- https://doi.org/10.1021/jo000810t
Abstract
A highly stereoselective sequence of reactions, based on the anti-selective SN2‘ addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having α-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the “alkylation” of sec- and tert-alkyl and aryl groups.Keywords
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