Collect. Czech. Chem. Commun. 2000, 65, 816-828

Stereoselective Synthesis of 2-Substituted Pyrrolidines

Sandrine Deloisya, Heiko Tietgenb and Horst Kunzb,*

a Université de Paris-Sud, ICMO, Laboratoire des Carbocycles, F-91405 Orsay cedex, France
b Institut für Organische Chemie, Universität Mainz, D-55099 Mainz, Germany


Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.

Keywords: Carbohydrates; Chiral auxiliaries; Homoallylamines; Electrophile-induced cyclization; Pyrrolidines; Nornicotine; Alkaloids; Enantioselective reactions.

References: 25 live references.