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Synfacts 2005(1): 0141-0141  
DOI: 10.1055/s-2005-872185
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Nitro-Mannich Reactions

Contributor(s): Mark Lautens, Y. Eric Fang
J. C. Anderson*, G. P. Howell, R. M. Lawrence, C. S. Wilson
University of Nottingham, UK
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Publication History

Publication Date:
23 September 2005 (online)

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Significance

This Cu(II)-catalyzed nitro-Mannich reaction afforded anti-β-nitroamines from p-methoxybenzylimines and TMS-nitropropanate. The products were obtained with generally good to excellent enantio- and diastereoselectivity and in good yields by using Cu(OTf)2 and a tert-Bu-BOX ligand. A range of aryl, heteroaryl and alkyl ald­imines worked well under these conditions. The product can be readily converted into synthetically useful 1,2-diamines through a SmI2 reduction in good yield.