An asymmetric nitro-Mannich reaction applicable to alkyl, aryl, and heterocyclic imines

作者:Anderson JC*; Howell GP; Lawrence RM; Wilson CS
来源:Journal of Organic Chemistry, 2005, 70(14): 5665-5670.
DOI:10.1021/jo050762i

摘要

A protocol for the enantioselective nitro-Mannich coupling between alkyl, aryl, and heterocyclic p-methoxybenzylimines and trimethylsilylnitropropanate catalyzed by a chiral Bu-t-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 beta-nitroamines are obtained in 70-94% enantiomeric excess in good yield and can be readily reduced to synthetically useful 1,2-diamines.

  • 出版日期2005-7-8