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Triflic Acid-Catalyzed Additions of 2-Alkoxycarbonyl Allylboronates to Aldehydes. Study of Scope and Mechanistic Investigation of the Reaction Stereochemistry

Tim G. Elford, Yuichiro Arimura, Siu Hong Yu and Dennis G. Hall*

*Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2G2, Email:

T. G. Elford, Y. Arimura, S. H. Yu, D. G. Hall, J. Org. Chem., 2007, 72, 1276-1284.

DOI: 10.1021/jo062151b

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A mechanistic investigation on the effect of substrate on stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes confirms the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access to β,γ-disubstituted five-membered ring lactones.

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ID: J42-Y2007-0510