91840-94-7Relevant academic research and scientific papers
Readily available ruthenium complex for efficient dynamic kinetic resolution of aromatic α-hydroxy ketones
Agrawal, Santosh,Martinez-Castro, Elisa,Marcos, Rocio,Martin-Matute, Belen
, p. 2256 - 2259 (2014/05/06)
A ruthenium complex formed from commercially available [Ru(p-cymene)Cl 2]2 and 1,4-bis(diphenylphosphino)butane catalyzes the racemization of aromatic α-hydroxy ketones very efficiently at room temperature. The racemization is fully compatible with a kinetic resolution catalyzed by a lipase from Pseudomonas stutzeri. This is the first example of dynamic kinetic resolution of α-hydroxy ketones at ambient temperature in which the metal and enzyme catalysts work in concert in one pot at room temperature to give quantitative yields of esters of α-hydroxy ketones with very high enantioselectivity.
Solution-phase synthesis and evaluation of tetraproline chiral stationary phases
Dai, Zhi,Ye, Guozhong,Pittman Jr., Charles U.,Li, Tingyu
experimental part, p. 329 - 338 (2012/05/20)
A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright
Lipase TL-mediated kinetic resolution of benzoin: Facile synthesis of (1R,2S)-erythro-2-amino-1,2-diphenylethanol
Aoyagi, Yutaka,Agata, Naoki,Shibata, Noriko,Horiguchi, Mai,Williams, Robert M.
, p. 10159 - 10162 (2007/10/03)
The lipase TL-mediated kinetic resolution of (±)-benzoin (1) proceeded to give the corresponding optically pure benzoin (R)-1. On the other hand, (S)-benzoin-O-acetate (5) could be hydrolyzed without epimerization to give (S)-benzoin (S)-1, under alkaline conditions. Further, (R)-1 was converted to (1R,2S)-2-amino-1,2-diphenylethanol (99:1 er) according to the procedure reported previously. (C) 2000 Elsevier Science Ltd.
Optical resolution method
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, (2008/06/13)
The present invention provides three optical resolution methods. The first aspect comprises the steps of adding an optically active bifunctional resolving reagent to a bifunctional compound to form a liquid material, precipitating crystals therefrom, and treating the crystals and the liquid material separately with an acidic material, a basic material, or a basic material and an acidic material, to obtain a pair of enantiomers of an optically active bifunctional compound. The second aspect comprises an optical resolution method by which one necessary enantiomer of a pair of enantiomers in an optically active bifunctional compound is exclusively obtained. The third aspect comprises a method for racemizing one unnecessary enantiomer of a pair of enantiomers in an optically active bifunctional compound which is formed by the optical resolution method of the present invention.
STEREOSELECTIVE CATALYTIC HYDROGENERATION OF alpha -HYDROXY KETOXIMES.
Harada,Shiono
, p. 1040 - 1045 (2007/10/02)
Two isomers (E and Z) of benzoin oxime and 2-hydroxy-1-phenyl-1-propanone oxime were catalytically hydrogenated by using palladium on charcoal and erythro amino alcohols were obtained in about 80% diastereomeric excess. The syn-anti isomerization of these oximes in the presence of palladium on charcoal was also studied in connection with the stereoselectivity of the catalytic hydrogenation of the oximes.
