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