Asymmetric Synthesis of Spirooxazolidinone Oxindoles by the Thiourea-Catalyzed Aldol Reaction of 2-Isocyanatomalonate Diesters

A tertiary amino-thiourea catalyzed asymmetric aldol reaction between 2-isocyanatomalonate esters and isatins has been achieved. Optical active spirooxazolidinone oxindole derivatives could be obtained with excellent yields (80%-96%) and enantioselectivities (67%-99% ee) under mild conditions, providing an updated example to apply isatins as the electrophile in the asymmetric aldol reaction with 2-isocyanatomalonate esters.

Automated summary

A tertiary amino-thiourea catalyzed asymmetric aldol reaction between 2-isocyanatomalonate esters and isatins has been achieved, leading to the formation of optically active spirooxazolidinone oxindole derivatives with excellent yields and enantioselectivities under mild conditions. This work provides an updated example of using isatins as electrophiles in the asymmetric aldol reaction with 2-isocyanatomalonate esters.