title: Enantioselective allylation of beta,gamma-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes.
abstract: [reaction: see text] 2-Vinyloxiranes have been found to be excellent surrogates to beta,gamma-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)(3), are effectively trapped by the chiral allylating agents based on alpha-pinene, affording bishomoallylic alcohols in high yield and excellent selectivity.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada. mlautens@alchemy.chem.utoronto.ca
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Maddess
authors.forename: Effiette L O
authors.initials: EL
authors.lastname: Sauer
authors.forename: Stéphane G
authors.initials: SG
authors.lastname: Ouellet