Copper-Catalyzed Asymmetric Michael Reactions with α-Amino Acid Amides: Synthesis of an Optically Active Piperidine Derivative

Quaternary stereocenters are obtained at room temperature in copper-catalyzed asymmetric Michael reactions with α-amino acid amides as chiral auxiliaries. L-Valine diethylamide was applied as a chiral auxiliary, and an optically active piperidine derivative was prepared with 97% ee. The optical purity of the product was established by GLC after cyclization to a hexahydroisoquinolonecarboxylate. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)