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.