Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles

Abstract

Asymmetric cascade double Michael additions to construct 2'-substituted 3,3'-spirooxindoles by using a chiral guanidine organocatalyst has been developed. A series of spirooxindole derivatives containing dihydrofuran or pyrrolidine subunits were obtained with good to excellent diastereo- and enantioselectivities. The method showed great tolerance of a number of aromatic and aliphatic alkynones. The strategy gave access to the asymmetric synthesis of (-)-salacin for the first time.