title: A Diels-Alder approach to the stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines.
abstract: [structures: see text] A stereoselective synthesis of 2,3,5,6-tetra- and 2,3,4,5,6-pentasubstituted piperidines was achieved from oxidative cleavage of 2-aza-bicyclo[2.2.2]octene Diels-Alder adducts derived from N-protected 2-methyl-1,2-dihydropyridine. A chiral auxiliary mediated asymmetric synthesis of the pentasubstituted piperidine is also demonstrated. This methodology incorporates orthogonal protecting groups, thus providing a piperidine scaffold with easily modified points of diversity.
authors.affiliation: Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
authors.forename: Marcelo
authors.initials: M
authors.lastname: Sales
authors.forename: André B
authors.initials: AB
authors.lastname: Charette