Synthesis of Chiral Spiro[oxindole-3,2′-pyrrolidine] Derivatives Integrated with Spiro Indane-1,3-dione and Trifluoromethyl Group Pharmacophores via Organocatalyzed Asymmetric [3+2] Annulation

A mild and efficient organocatalyzed [3+2] cycloaddition of isatin-derived ketimines and 2-ylideneindane-1,3-diones has been realized. The resulting spiro[oxindole-3,2 '-pyrrolidine]s bearing both a spiro indane-1,3-dione motif and a trifluoromethyl group were obtained in high yields with good diastereo-and enantioselectivities.

Automated summary

A mild and efficient organocatalyzed [3+2] cycloaddition reaction between isatin-derived ketimines and 2-ylideneindane-1,3-diones has been achieved. The resulting spiro[oxindole-3,2'-pyrrolidine] compounds, containing both spiro indane-1,3-dione motif and a trifluoromethyl group, were obtained in high yields with good diastereo- and enantioselectivities.