Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey–Chaykovsky Reaction of Isatin Derived N‑tert-Butanesulfinyl Ketimines

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).我们开发了一种通用且直接的策略，通过靛红衍生的N-叔丁基亚磺酰酮亚胺的氮杂-Corey-Chaykovsky反应，实现手性螺环氮丙啶吲哚酮的合成，该反应具有优异的选择性，非对映选择性比（diastereomeric ratio, dr）为98:2至>99:1。本方法可用于合成手性3-取代螺环氮丙啶吲哚酮，其(2S,3S)构型选择性优于(2S,3R)构型。