Primary amines are used as intermediates for the synthesis of a variety of pharmaceutical products. The enantioselective synthesis of nonracemic amines is the most important method for the production of enantiopure drugs. Previously, we developed a higly enantioselective method for the synthesis of enantiopure amines by the reduction of O-benzyl oxime ethers with a spiroborate ester/borane system. Using 10% of the catalyst derived from diphenyl valinol and ethylene glycol, (R) and (S) naphtyl-1-ethylamines were obtained in good yield and excellent enantiopurity (>99% ee). Secondary hyperparathyroidism is a dangerous disease characterized by an excessive secretion of the parathyroid hormone due to low calcium levels in the body. Calcimimetic agents are new drugs, whose name reflects their major action: to mimic the effect of calcium on calcium receptors, and have the potential to control hyperparathyroidism. A new approach for the synthesis of novel class calcimimetic analogs from enantiopure amines will be presented. 

Asymmetric synthesis of primary amine and its conversion to new calcimimetic analogs

244th National Meeting (2012)

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