Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

Abstract

A highly efficient method for the enantioselective construction of dispirocyclic compounds has been developed by the squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 2,3-dioxopyrrolidines with 3-chlorooxindoles. The corresponding chiral dispiro[indoline-3,1′-cyclopropane-2′,3′′-pyrrolidine]-2,4′′,5′′-triones were obtained in high yields with excellent stereoselectivities (up to 94% yield, >25 : 1 dr and >99% ee). Furthermore, a gram-scale experiment confirmed the reliability of the current reaction and further effective transformation of the product has been realized.