Boron containing chiral Schiff bases: Synthesis and catalytic activity in asymmetric transfer hydrogenation (ATH) of ketones

Publication date: 15 January 2020Source: Journal of Molecular Structure, Volume 1200Author(s): Salih Paşa, Nevin Arslan, Nermin Meri̇ç, Cezmi Kayan, Murat Bingül, Feyyaz Durap, Murat AydemirAbstractAsymmetric Transfer Hydrogenation (ATH) has been an attractive way for the reduction of ketones to chiral alcohols. A great number of novel and valuable synthetic pathways have been achived by the combination usage of organometallic and coordination chemistry for the production of important class of compounds and particularly optically active molecules. For this aim, four boron containing Schiff bases were synthesized by the reaction of 4-formylphenylboronic acid with chiral amines. The boron containing structures have been found as stable compounds due to the presence of covalent B–O bonds and thus could be handled in laboratory environment. They were characterized by 1H NMR and FT-IR spectroscopy and elemental analysis and they were used as catalyst in the transfer hydrogenation of ketones to the related alcohol derivatives with high conversions (up to 99%) and low enantioselectivities (up to 22% ee).Graphical abstract
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research