Enantioselective Synthesis of alpha-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols

摘要

The enantioselective copper-catalyzed oxidative desymmetrization for the synthesis of chiral alpha-substituted serine derivatives is reported. The combination of Cu(OTf)(2)/(R,R)-PhBOX catalyst system, N-bromosuccinimide, and MeOH enables us to provide chiral alpha-substituted serines from N-2-methylbenzoylprotected 2-amino-1,3-diols through a simple procedure at room temperature under an air atmosphere. A variety of alpha-substituent including aryl and heteroaryl groups were tolerated in this method, and the corresponding chiral serine derivatives were obtained in good to high yields with high enantioselectivities.