(2 S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-catalyzed efficient stereoselective michael addition of cyclohexanone and cyclopentanone to nitroolefins

Abstract

(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 β-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various γ-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.