3113-98-2Relevant articles and documents
Effects of triethylamine in asymmetric reduction using oxazaborolidine reagents
Cai,Tschaen,Shi,Verhoeven,Reamer,Douglas
, p. 3243 - 3246 (1993)
In the presence of triethylamine, the reduction of ketones using stoichiometric amounts of oxazaborolidine-borane complex (OAB·BH'3) shows increased enantioselectivity.
Production of chiral alcohols from racemic mixtures by integrated heterogeneous chemoenzymatic catalysis in fixed bed continuous operation
Carceller, Jose Miguel,Climent, Maria J.,Corma, Avelino,Iborra, Sara,Mifsud, Maria
, p. 2767 - 2777 (2020/06/17)
Valuable chiral alcohols have been obtained from racemic mixtures with an integrated heterogeneous chemoenzymatic catalyst in a two consecutive fixed catalytic bed continuous reactor system. In the first bed the racemic mixture of alcohols is oxidized to the prochiral ketone with a Zr-Beta zeolite and using acetone as the hydrogen acceptor. In the second catalytic bed the prochiral ketone is stereoselectively reduced with an alcohol dehydrogenase (ADH) immobilized on a two dimensional (2D) zeolite. In this process, the alcohol (isopropanol) formed by the reduction of acetone in the first step reduces the cofactor in the second step, and the full reaction cycle is in this way internally closed with 100% atom economy. A conversion of about 95% with ~100% selectivity to either the (R) or the (S) alcohol has been obtained for a variety of racemic mixtures of alcohols.
Boron containing chiral Schiff bases: Synthesis and catalytic activity in asymmetric transfer hydrogenation (ATH) of ketones
Pa?a, Salih,Arslan, Nevin,Meri??, Nermin,Kayan, Cezmi,Bingül, Murat,Durap, Feyyaz,Aydemir, Murat
, (2019/09/19)
Asymmetric 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).