A new method for the preparation of Mannich bases from 2-acylaziridines using silyllithium reagents has been developed. The reaction is believed to proceed via Brook rearrangement assisted by opening of the adjacent aziridine. A series of 2-acylaziridines were reacted with methyldiphenylsilyllithium to form the corresponding Mannich bases in good to excellent yield. 2-Acylazridines with an N-tosyl group produced the highest yield of Mannich base after the reduction.

Preparation of Mannich bases from 2-acylaziridines using silyllithium reagents

245th National Meeting (2013)

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