1073106-05-4Relevant articles and documents
Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes
Aga, Mushtaq A.,Kumar, Brijesh,Rouf, Abdul,Shah, Bhahwal A.,Taneja, Subhash C.
, p. 2639 - 2641 (2014)
The first report of natural l-vasicine as tridentate chiral ligand for the enantioselective addition of diethylzinc to a variety of aliphatic and aromatic aldehydes is described. The ligand generates R-isomer of the secondary alcohols upto 98% ee. The qui
Candida tenuis xylose reductase catalyzed reduction of aryl ketones for enantioselective synthesis of active oxetine derivatives
Vogl, Michael,Brecker, Lothar,Kratzer, Regina,Nidetzky, Bernd
, p. 847 - 853,7 (2020/07/31)
Candida tenuis xylose reductase shows high catalytic efficiencies in carbonyl reduction of acetophenone and 1-phenyl-1-propanone derivatives. The quite low substrate solubility in aqueous buffer systems is circumvented by addition of methanol or by two-phase solvent systems. In the latter, methanol improves the substrate phase transfer as solvent mediator and leads to reasonable space/time yields. Resulting enantiomerically pure chiral alcohols are key intermediates for synthesis of active pharmaceutical ingredients. (R)-Atomoxetine is exemplarily synthesized in four steps, and the further use for generation of other oxetine derivatives and a polo-like kinase 1 inhibitor are discussed. Copyright
A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes
Liu, Chang-Lu,Wei, Chang-Yong,Wang, Shi-Wen,Peng, Yun-Gui
experimental part, p. 921 - 928 (2012/06/17)
Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework.