Preparation of homoallylic homopropargylic alcohols from 2-vinyloxiranes.
Beta,gamma-unsaturated aldehydes generated in situ by treatment of 2-vinyloxiranes with a catalytic amount of Sc(OTf)(3) or BF.OEt(2) are effectively trapped by B-allenyl-9-BBN to afford homoallylic homopropargylic alcohols in high yield. An enantioselective version has been demonstrated, and a convenient synthesis of 9-allenyl-9-BBN is described. [reaction: see text]
Maddess
Matthew L
ML
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Lautens
Mark
M