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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 , Email: mlautensalchemy.chem.utoronto.ca

L. Wang, M. L. Maddess, M. Lautens, J. Org. Chem., 2007, 72, 1822-1825.

DOI: 10.1021/jo062107w (free Supporting Information)


Abstract

Trapping of β,γ-alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF3ˇOEt2, by a variety of allyl nucleophiles affords homopropargylic homoallylic alcohols in good yield and selectivity. Subsequent enyne metathesis gives functionalized vinylcyclopentenols.

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Key Words

Homoallylic Alcohols, Homopropargylic Acohols, Enyne Metathesis, Microwave Synthesis, Cyclopentanols, Cyclopentenes


ID: J42-Y2007-0790