title: Morita-Baylis-Hillman reaction and cyclization of 1-(p-toluenesulfonyl)-1,3-butadiene with aldimines.
abstract: [reaction: see text] Aldimines 2 underwent Morita-Baylis-Hillman reaction with 1-(p-toluenesulfonyl)-1,3-butadiene (3) in the presence of 3-hydroxyquinuclidine (HQD) to afford adducts 4. The E-isomers of the products cyclized to the corresponding functionalized piperidines 8 under base-catalyzed conditions. Simultaneous equilibration of (E)-4 and (Z)-4 was effected by photoisomerization to improve the efficiency of the cyclization.
authors.affiliation: Department of Chemistry, University of Calgary, Calgary, AB, Canada, T2N 1N4. tgback@ucalgary.ca
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Back
authors.forename: Danica A
authors.initials: DA
authors.lastname: Rankic
authors.forename: Jovina M
authors.initials: JM
authors.lastname: Sorbetti
authors.forename: Jeremy E
authors.initials: JE
authors.lastname: Wulff