Synfacts 2007(12): 1270-1270  
DOI: 10.1055/s-2007-991381
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Allylic Amination with Ammonia Equivalents

Contributor(s): Mark Lautens, Frédéric Ménard
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig*
University of Illinois, Urbana, and Yale University, New Haven, USA
Further Information

Publication History

Publication Date:
22 November 2007 (online)


Building on their extensive studies of asymmetric iridium-catalyzed allylic aminations, the authors reported a practical method to synthesize primary allylic amine precursors 3 and 6. The reaction makes use of easily handled amine salts and low catalyst loadings to obtain the products in high ee. Further, a direct enantioselective allylation with ammonia was reported for the first time with a metal catalyst. The reaction yielded the secondary amine 7, which is a useful precursor for the synthesis of C 2-symmetric pyrrolidines.