The preparation of new chiral amino alcohols derivatives and investigation of their catalytic activity in enantioselective borane reduction of prochiral ketones

Enantioselective synthesis of organic compounds is one of the major interests of most researchers. Single enantiomer form of synthetic chiral molecules has a wide application field such as pharmaceutics, optical and electronic devices, as a component of polymers with new features and as probe with biological function. Therefore, synthesis of a single enantiomeric form of chiral organic compounds or mixtures of high enantiomeric purity is one of the interesting subjects of organic chemistry. Reduction of prochiral ketones to enantiomerically enriched secondary alcohols is a significant transformation in synthetic organic chemistry.In this study, first, acid group of salicylic acid is activated by thionyl chloride to give acid chloride and then totally 7 multi coordinated new ? -hydroxy amide derivative ligands synthesized by reacting the acid chlorides with chiral amino alcohols having aliphatic and aromatic groups at their stereogenic centers. Their borane complexes were prepared in appropriate THF medium by reacting the ligands with BH3.Me2S. Catalytic activities of these ligands were investigated in enantioselective reduction of various prochiral ketones depending on electronic and steric effects.Key Words: Enantioselective reduction, ß-hydroxy amides, Prochiral ketones, BH3.Me2S.