Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry |
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Authors: | Elford Tim G Arimura Yuichiro Yu Siu Hong Hall Dennis G |
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Affiliation: | Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2. |
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Abstract: | 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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