Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines.

A highly efficient N,N'-dioxide-Zn(II) complex catalytic system for the asymmetric Diels-Alder reaction of Brassard-type diene with methyleneindolines was developed. The optically pure spiro[cyclohex[3]ene-1,3'-indoline]-1'-carboxylate-2, 2'-dione derivatives containing three stereocenters were obtained in moderate yields with 98% to >99% ee in a stereospecific manner.