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:
mlautens
alchemy.chem.utoronto.ca
L. Wang, M. L. Maddess, M. Lautens, J. Org. Chem., 2007, 72, 1822-1825.
DOI: 10.1021/jo062107w
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.
see article for more examples
Key Words
Homoallylic Alcohols, Homopropargylic Acohols, Enyne Metathesis, Microwave Synthesis, Cyclopentanols, Cyclopentenes
ID: J42-Y2007-0790
