title: Direct vinylogous Mannich-type reactions via ring opening and rearrangement of vinyloxiranes.
abstract: [reaction: see text] The first synthetic application of 2-methyl-2-vinyloxirane as a masked dienolate has been successfully demonstrated in the direct vinylogous Mannich-type reaction with an alpha-imino ester as an electrophile. The Mannich adduct was a useful intermediate en route to cis-5-substituted pipecolinic acid ethyl ester under simple hydrogenation conditions.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6. mlautens@chem.utoronto.ca
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
authors.forename: Eiji
authors.initials: E
authors.lastname: Tayama
authors.forename: Duy
authors.initials: D
authors.lastname: Nguyen