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Synfacts 2009(4): 0412-0412  
DOI: 10.1055/s-0028-1087907
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydrogenation of Cyclic Enamines

Contributor(s): Mark Lautens, Praew Thansandote
G.-H. Hou, J.-H. Xie, P.-C. Yan, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

The authors report very mild conditions for the asymmetric hydrogenation of cyclic enamines. Using chiral iridium complexes of phosphoramidites, a variety of enamines in five-membered rings can be hydrogenated in good yields and enantioselectivities. The ee values are lower for six-membered rings, although an excellent value is obtained for the hydrogenation of a precursor to the alkaloid crispine A.