Synfacts 2006(11): 1161-1161  
DOI: 10.1055/s-2006-949486
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Mn-Mediated Radical Diastereoselective Alkylation of N-Acylhydrazones

Contributor(s): Paul Knochel, Andrei Gavryushin
G. K. Friestad*, J.-C. Marié, Y. S. Suh, J. Qin
University of Iowa, Iowa City and University of Vermont, Burlington, USA
Further Information

Publication History

Publication Date:
24 October 2006 (online)

Significance

Enantioselective radical addition to imines represents a mild useful method for the asymmetric amine synthesis. The authors developed an elegant, versatile protocol for the Mn-carbonyl-promoted diastereoselective addition of primary and secondary alkyl radicals to chiral hydrazones. This method allows a simple enantio­selective preparation of functionalized amines and hydrazines with a chiral center at the α-carbon. The procedure is relatively simple, good yields and very high diastereoselectivities are achieved in most cases.