title: Alkylation of phenylglycinol-derived oxazolopiperidone lactams. Enantioselective synthesis of beta-substituted piperidines.
abstract: The stereochemical outcome of the alkylation of a variety of phenylglycinol-derived oxazolopiperidone lactams is studied. The influence of the configuration of the C-8a stereocenter and the effect of the substituents at the C-8 and C-8a positions on the stereoselectivity of the reaction are discussed. The synthetic utility of these alkylation reactions is illustrated with the synthesis of cis and trans 3,5-disubstituted, 2,5-disubstituted, and 2,3,5-trisubstituted enantiopure piperidines, and the indole alkaloids 20R- and 20S-dihydrocleavamine.
authors: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@ub.edu
authors: Mercedes
authors: M
authors: Amat
authors: Carmen
authors: C
authors: Escolano
authors: Oscar
authors: O
authors: Lozano
authors: Arantxa
authors: A
authors: Gómez-Esqué
authors: Rosa
authors: R
authors: Griera
authors: Elies
authors: E
authors: Molins
authors: Joan
authors: J
authors: Bosch