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

Author:
Hajra, Saumen, Aziz, Sk Mohammad, Jana, Bibekananda, Mahish, Prosenjit, Das, Dhiraj
Source:
Organic letters 2016 v.18 no.3 pp. 532-535
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, 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).
Agid:
5792305