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Asymmetric Allylic Amination with Ammonia Equivalents
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig*
University of Illinois, Urbana, and Yale University, New Haven, USA
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.