Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

Abstract

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes.

The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxindole compounds.

Keywords

• organocatalysis
• spirocompounds
• oxindole
• cascade reaction