(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins

(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from L-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to beta-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various gamma-nitro carbonyl compounds in high yield (up to 97%) with excellent stereoselectivity (up to >99:1 dr and >99% ee) without the use of any additive.