Chemoselective Allene Aziridination via Ag(I) Catalysis

J. W. Rigoli, C. D. Weatherly, B. T. Vo, R. Van Hoveln, S. E. Neale, J. M. Schomaker
Organic Letters
15 (2), 290-293
Published while none of the authors were employed at the CMM


Allene aziridination generates useful bicyclic methylene aziridine scaffolds that can be flexibly transformed into a range of stereochemically complex and densely functionalized amine-containing stereotriads. The scope of this chemistry has been limited by the poor chemoselectivity that often results when typical dinuclear Rh(II) catalysts are employed with homoallenic carbamates. Herein, Ag(I) catalysts that significantly improve the scope and yield of bicyclic methylene aziridines that can be prepared via allene aziridination are described.