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Synfacts 2011(4): 0394-0394  
DOI: 10.1055/s-0030-1259666
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Calcium-Catalyzed Enantioselective Electrophilic Amination of Enamides

Contributor(s): Hisashi Yamamoto, Jiajing Tan
F. Drouet, C. Lalli, H. Liu, G. Masson*, J. Zhu*
Institut de Chimie des Substances Naturelles, France and Ecole Polytechnique Fédérale de Lausanne, Switzerland
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Publikationsdatum:
18. März 2011 (online)

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Significance

In this paper, the authors report a highly efficient nucleophilic addition of enamides to azodicaboxylate catalyzed by a nonracemic calcium bis(phosphate) complex. The enantioenriched 1,2-hydrazinoimines can be further hydrolyzed or reduced, giving the 2-hydrazino ketones or syn-1,2-disubstituted 1,2-diamines derivatives in high yields and excellent enantioselectivities.