Synthesis of chiral ß-hydroxy amide derivatives and investigation of their catalytic activity in enantioselective reduction of prochiral ketones in the presence of boran dimetil

Main propose synthesis of modern organic chemistry is to develop easily obtainable catalyst by simple methods. Optically active compounds are important building blocks for synthesis of pharmaceutics, pesticides, odorants, nice smelling aromates and liquid crystals.Catalytic enantioselective reaction is an important tool in synthesis of chiral molecules. Important auxiliary agents and ligands as well as chiral ß-amino alcohols are used as building blocks for biologically active molecules in asymmetric synthesis. Optically active alcohols obtained from asymmetric reduction of ketones serve as a lot of enantiomerically pure compounds including biologically active natural substance.In the present study 3-hydroxy-2-naftoic acid was treated first 1-hydroxybenzotriazolmonohydrate (HOBt) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimidohydrochloride (EDCI) and then it was reacted with a variety of chiral ß-hydroxy amino alcohols to obtain 7 new multi coordinate ß-hydroxy amide derivatives. These ligands were treated with BH3S(Me)2 to give borane complexes in dry THF medium. Catalytic activity of these ligands were evaluated by electronically and sterically different prochiral ketones.