Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

Letian Wang, Matthew L. Maddess, and Mark Lautens*
80 St. George Street, Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada mlautens@alchemy.chem.utoronto.ca
J. Org. Chem., 2007, 72 (5), pp 1822–1825
DOI: 10.1021/jo062107w
Publication Date (Web): February 7, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

β,γ-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF3·OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.

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History

  • Published In Issue March 02, 2007
  • Received October 11, 2006

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