3-4'-Bipiperidines via sequential [4 + 4]-[3,3]-retro-Mannich reactions.
An approach to assembling unsymmetrically coupled piperidines is described, involving initial [4 + 4] photocycloaddition of 2-pyridones, followed by Cope rearrangement and retro-Mannich reaction. In these reactions, four stereogenic centers set during cycloaddition are relayed or erased during the subsequent steps. Two methods for retro-Mannich reaction are demonstrated.
Chen
Peiling
P
Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.
Carroll
Patrick J
PJ
Sieburth
Scott McN
SM