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
J. Org. Chem., 2007, 72 (4), pp 1276–1284
DOI: 10.1021/jo062151b
Publication Date (Web): January 20, 2007
Copyright © 2007 American Chemical Society
*

 Corresponding author. Tel.:  (780) 492-3141. Fax:  (780) 492-8231.

, dennis.hall@ualberta.ca

Abstract

Abstract Image

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 β,γ-disubstituted five-membered ring lactones with an exo-methylene at the α-position.

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History

  • Published In Issue February 16, 2007
  • Received October 17, 2006

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