104863-49-2Relevant articles and documents
Copper(I) hydride-catalyzed asymmetric hydrosilylation of heteroaromatic ketones
Lipshutz, Bruce H.,Lower, Asher,Noson, Kevin
, p. 4045 - 4048 (2002)
(formula presented) In situ generation of CuH ligated by Takasago's new nonracemic ligand, DTBM-SEGPHOS, leads to an especially reactive reagent capable of effecting asymmetric hydrosilylation of heteroaromatic (H) ketones under very mild conditions. PMHS serves as an inexpensive source of hydride. Substrate-to-ligand ratios on the order of 2000:1 are employed.
ENANTIOSELECTIVITY IN MICROBIAL REDUCTION OF PROCHIRAL CARBONYL GROUPS: A WIDE SCREENING TOWARD R AND S ISOMERS
Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola,Poli, Silvia,et al.
, p. 243 - 246 (1991)
More than fifty yeast and mould strains were tested in the reduction of 2-acylthiazoles 1-5.The possibility of obtaining R or S enantiomers with high enantioselectivities from various species and strains is described.
General asymmetric hydrogenation of hetero-aromatic ketones
Ohkuma, Takeshi,Koizumi, Masatoshi,Yoshida, Makoto,Noyori, Ryoji
, p. 1749 - 1751 (2000)
(matrix presented) Het = hetero-aromatic ring (R,R)-Ru cat = trans-RuCl2[(R)-xylbinap][(R)-daipen] trans-RuCl2[(R)-xylbinap][(R)-daipen] or the S,S complex acts as an efficient catalyst for asymmetric hydrogenation of hetero-aromatic ketones. The hydrogenation proceeds with a substrate-to-catalyst molar ratio of 1000-40000 to give chiral alcohols in high ee and high yield. The enantioselectivity appears to be little affected by the properties of the hetero-aromatic ring. This method allows for asymmetric synthesis of duloxetine, an inhibitor of serotonin and norepinephrine uptake carriers.
Iron catalyzed asymmetric hydrogenation of ketones
Li, Yanyun,Yu, Shenluan,Wu, Xiaofeng,Xiao, Jianliang,Shen, Weiyi,Dong, Zhenrong,Gao, Jingxing
supporting information, p. 4031 - 4039 (2014/04/03)
Chiral molecules, such as alcohols, are vital for the manufacturing of fine chemicals, pharmaceuticals, agrochemicals, fragrances, and novel materials. These molecules need to be produced in high yield and high optical purity and preferentially catalytically. Among all the asymmetric catalytic reactions, asymmetric hydrogenation with H2 (AH) is the most widely used in the industry. With few exceptions, these AH processes use catalysts based on the three critical metals, rhodium, ruthenium, and iridium. Herein we describe a simple, industrially viable iron catalyst that allows for the AH of ketones, a process currently dominated by ruthenium and rhodium catalysts. By combining a chiral, 22-membered macrocyclic ligand with the cheap, readily available Fe 3(CO)12, a wide variety of ketones have been hydrogenated under 50 bar H2 at 45-65 C, affording highly valuable chiral alcohols with enantioselectivities approaching or surpassing those obtained with the noble metal catalysts. In contrast to AH by most noble metal catalysts, the iron-catalyzed hydrogenation appears to be heterogeneous.
Kinetic resolution of racemic 1-heteroarylalkanols by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst
Shiina, Isamu,Ono, Keisuke,Nakata, Kenya
supporting information; experimental part, p. 147 - 149 (2011/04/14)
A variety of optically active 1-heteroarylalkanols and their esters, which include heteroaromatic moieties, such as 2-furyl, 2-thienyl, 3-thienyl, 2-thiazoyl, 2-benzothiazoyl, and 2-benzoxazoyl groups, are efficiently produced by a novel asymmetric esterification. The transition states that form the desired (R)- esters from the (R)-1-heteroarylalkanols are determined by DFT calculations, and the structural features of these transition states are systematically discussed.
MICROBIOLOGICAL SYNTHESIS OF VARIOUSLY PROTECTED L-GLYCERALDEHYDES IN HIGH OPTICAL PURITY
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 3547 - 3550 (2007/10/02)
Variously protected L-glyceraldehydes have been enantioselectively synthesized through a sequence involving acylation of formylanion equivalents with glycolic acid derivatives followed by baker's yeast mediated reduction of the resulting ketones.
