Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey–Chaykovsky Reaction of Isatin Derived <i>N-tert</i>-Butanesulfinyl Ketimines

Abstract

A general and direct strategy for the synthesis of chiral spiro-aziridine oxindoles has been developed via an aza-Corey-Chaykovsky reaction of isatin-derived N-tert-butanesulfinyl ketimines with excellent selectivity (dr = 98:2 to >99:1). The method is explored for the synthesis of chiral 3-substituted spiro-aziridine oxindoles with high (2S,3S)-selectivity over (2S,3R).