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Synfacts 2007(10): 1056-1056  
DOI: 10.1055/s-2007-963856
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioenriched Vinylic Diamines by Asymmetric Allylic Amination

Contributor(s): Mark Lautens, Michael Langer
B. M. Trost*, D. R. Fanrick, T. Brodmann, D. T. Stiles
Stanford University, USA
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Allylic alkylations and aminations are versatile methods to generate synthetically useful compounds. Racemic aziridines can be converted via dynamic kinetic resolution (DYKAT) into enantioenriched allylic diamines. In this work, the direct products of the asymmetric amination undergo subsequent acyl migration of the more electrophilic acyl group. Chiral diamines are produced with differentiated amines. The methodology is used in the synthesis of the protein kinase inhibitor balanol.