American Chemical Society
jo050762i_si_001.cif (18.89 kB)

An Asymmetric Nitro-Mannich Reaction Applicable to Alkyl, Aryl, and Heterocyclic Imines

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posted on 2005-07-08, 00:00 authored by James C. Anderson, Gareth P. Howell, Ron M. Lawrence, Claire S. Wilson
A protocol for the enantioselective nitro-Mannich coupling between alkyl, aryl, and heterocyclic p-methoxybenzylimines and trimethylsilylnitropropanate catalyzed by a chiral tBu-BOX Cu(II) catalyst is described. It uses the lowest reported loading of commercially available metal catalyst and chiral ligand, and gives the highest yields and selectivities for a broad substrate range including nonaromatic aldimines. The resultant β-nitroamines are obtained in 70−94% enantiomeric excess in good yield and can be readily reduced to synthetically useful 1,2-diamines.