Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 4, Pages 1276-1284Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo062151b
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The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechanistic investigation is described so as to confirm the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access to beta,gamma-disubstituted five-membered ring lactones with an exo-methylene at the alpha-position.
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