Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines

Abstract

This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented.

Keywords

• spirooxindoles
• organocatalysis
• azetidines
• cinchona-based catalysts