Enantioselective synthesis of α-amino-γ-sulfonyl phosphonates with a tetrasubstituted chiral α-carbon via quinine-squaramide-catalyzed michael addition of nitrophosphonates to vinyl sulfones

Article abstract of DOI:10.1002/adsc.201300224

α-Nitro-γ-sulfonyl phosphonates with a key tetrasubstituted chiral α-carbon center have been synthesized for the first time in high yield and enantioselectivity through a quinine-squaramide-catalyzed conjugate addition of α-nitro phosphonates to aryl vinyl sulfones. Representative examples presented here for the transformation of nitrosulfonyl phosphonates to aminosulfonyl phosphonates, alkylation at the α-position of the sulfonyl group followed by desulfonation and scale-up of the conjugate addition highlight the practical applications of the methodology. Copyright