New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions

Abstract

The construction of quaternary stereocenters with 95–99% ee at ambient temperatures can be achieved by a copper-catalyzed Michael reaction with the application of α-amino acid amides as chiral auxiliaries [Eq. (1)]. These amides can be obtained in a few steps from the α-amino acids with standard transformations and, after the Michael reaction, they can be quantitatively recovered. Exclusion of water and oxygen is not necessary.