A facile base-promoted domino Michael/O-alkylation reaction for the construction of succinimide-substituted 3(2H)-furanones

Abstract

A novel base-promoted domino Michael/O-alkylation reaction of maleimides with γ-halogenated-β-ketoesters is described. A variety of new succinimide-substituted 3(2H)-furanones were obtained in excellent yields (up to 96%) under simple and mild conditions. The structure of the new compound 3a was determined by singlecrystal X-ray analysis and a reaction pathway is proposed.

Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine

“…These fused chiral products might show higher or new biological activities. Recently, we reported the same transformation in racemic version catalyzed by Et 3 N. 17 As a part of our continuing interests in the construction of more complex and novel drug candidates, 18 herein, we wish to report the rst asymmetric domino Michael/O-alkylation reaction of g-halogenated-b-ketoesters with maleimides catalyzed by simple, cheap, commercially available cinchona alkaloids to access a new range of chiral succinimide substituted 3(2H)furanones ( Fig. 1).…”