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Synfacts 2009(9): 1013-1013  
DOI: 10.1055/s-0029-1217626
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Nucleophilic Addition of Samarium Enolates to Imines

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
J. M. ConcellÓn*, H. RodrÍguez-Solla, C. Simal
Universidad de Oviedo, Spain
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

This paper reports an addition of samarium enolates derived from esters and amides to imines as an alternative to conventional metal enolate addition. The corresponding β-amino esters and amides were obtained in good to high yields. Furthermore, an enantiopure 3,4-diamino ester could be obtained from the addition of samarium enolate to enantiopure imine 1 with very high diastereoselectivity.