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Synfacts 2009(11): 1231-1231  
DOI: 10.1055/s-0029-1218131
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Monoallylation of Ammonia

Contributor(s): Mark Lautens, Jane Panteleev
M. J. Pouy, L. M. Stanley, J. F. Hartwig*
University of Illinois, Urbana and Yale University, New Haven, USA
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The successful utilization of ammonia in allylation reactions has little precedent (see: T. Nagano, S. Kobayashi J. Am. Chem. Soc. 2009, 131, 4200). The authors disclose a more general mono-allylation of ammonia through the development of an iridium-phosphoramidite complex which is stable to a large excess of the simple amine. The authors report a good variety of chiral amine products in high enantioselectivities and moderate yields.