Experimental study demonstrates the synthesis of spirooxindoles from amines and isatins, highlighting an atypical hydride shift mechanism.
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.
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Ramakumar et al. (2017) studied this question.
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