Morita-Baylis-Hillman reaction and cyclization of 1-(p-toluenesulfonyl)-1,3-butadiene with aldimines.
[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.
Back
Thomas G
TG
Department of Chemistry, University of Calgary, Calgary, AB, Canada, T2N 1N4. tgback@ucalgary.ca
Rankic
Danica A
DA
Sorbetti
Jovina M
JM
Wulff
Jeremy E
JE