One-Pot Enantioselective Synthesis of 2-Pyrrolidinone Derivatives Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter.

Abstract

A new methodology for the one-pot enantioselective construction of 2-pyrrolidinone derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter at the 4-position has been described. This strategy combines an organocatalytic conjugate addition of nitroalkanes to isatin-derived α-trifluoromethyl acrylates and a reduction/lactamization process, affording the corresponding products in moderate to high yields (50-95%) with generally excellent stereoselectivities (up to 96% ee and >20:1 dr).