Synfacts 2011(5): 0515-0515  
DOI: 10.1055/s-0030-1259828
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Synthesis of Homoallylic Amines Using C 1-Symmetric NHCs

Contributor(s): Mark Lautens, Hasnain A. Malik
E. M. Vieira, M. L. Snapper*, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
15 April 2011 (online)

Significance

The authors disclose an enantio­selective Cu-catalyzed method for the synthesis of homoallylic amines using allylboron reagents and imines. Although there is plethora of chemical transformations for the asymmetric synthesis of chiral homoallyl amines, many require stoichiometric quantities of costly or highly toxic reagents and/or catalysts. This report entails a general and highly enantioselective protocol for the synthesis of chiral homoallyl amines using cheap and benign Cu catalysts that employ C 1-symmetric NHCs. A model for asymmetric induction is proposed to rationalize enantioselectivity trends.