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: dennis.hall
ualberta.ca
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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Abstract
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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Key Words
ID: J42-Y2007-0510
