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

Affiliation

School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, P. R. China. [Email]

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.

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