Organic Letters
Organic Letters
5 years ago

Synthesis of Spirooxindoles via the tert-Amino Effect

Synthesis of Spirooxindoles via the tert-Amino Effect
James J. Partridge, Jon A. Tunge, Kinthada Ramakumar, Tapan Maji
A new method is developed for the synthesis of spirooxindoles from amines and isatins via C–H functionalization. The reaction leverages the tert-amino effect to form an enolate–iminium intermediate via [1,5]-hydride shift followed by cyclization. Interestingly the hydride migrates to the N atom of a C═N, which is atypical for hydride additions to imines.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01752

DOI: 10.1021/acs.orglett.7b01752

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