Synfacts 2008(8): 0870-0870  
DOI: 10.1055/s-2008-1077891
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Mn-Mediated Radical Addition of Alkyl Iodides to Ketimines

Contributor(s): Paul Knochel, Andrei Gavryushin
G. K. Friestad*, A. Ji
University of Iowa, Iowa City, USA
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

The radical addition of alkyl iodides to ketimines offers a direct access to α,α-disubstituted amino- and hydrazoesters. The reaction proceeds with good yields in the case of primary and secondary alkyl iodides. The use of an oxazolidinone as a chiral auxiliary allows a highly diastereoselective preparation of rather difficult to access α,α-disubstituted amino acid derivatives, which are extremely interesting compounds for the synthesis of non-natural peptides.