Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols

Abstract

A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinylsulfinyl-containing amino alcohols 1−3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)