13113-71-8Relevant academic research and scientific papers
Optical Resolution of 2-Amino-1,2-diphenylethanol by Preferential Crystallization and Its Utilization in Fractional Crystallization and Enantioselective Reduction of Prochiral Ketones
Saigo, Kazuhiko,Ogawa, Shigeo,Kikuchi, Shigetoshi,Kasahara, Atsushi,Nohira, Hiroyuki
, p. 1568 - 1573 (1982)
(-/+)-erythro-2-Amino-1,2-diphenylethanol prepared from benzoin oxime by catalytic reduction was successfully resolved into pair of optically active forms by preferential crystallization.The optically active amino alcohol was found to be useful as a basic resolving agent for optical resolution of tartaric acid, trans-2,3-oxiranedicarboxylic acid, 2-hydroxy-2-phenylpropionic acid, and 3-endo-benzamido-5-norbornene-2-endo-carboxylic acid.Chiral hydrides prepared from lithium aluminium hydride and optical active threo- and erythro-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in the 26-72percent optical purities.
Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol
Kodama, Koichi,Nagata, Jun,Kurozumi, Nobuhiro,Shitara, Hiroaki,Hirose, Takuji
, p. 460 - 466 (2017)
The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.
Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3- dioxolan-4-ones
Misaki, Tomonori,Ureshino, Satoko,Nagase, Ryohei,Oguni, Yumiko,Tanabe, Yoo
, p. 500 - 504 (2006)
A practical method for the synthesis of optically pure α- alkylmandelic acids 1 is described. The present improved robust method involved two reactions: a mild, convenient, stereo-selective preparation of chiral cis-5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones, 9a-c, and highly diastereoselective alkylation of 9a-c, followed by the hydrolysis.
Entrapment of a chiral cobalt complex within silver: A novel heterogeneous catalyst for asymmetric carboxylation of benzyl bromides with CO2
Yang, Heng-Pan,Yue, Ying-Na,Sun, Qi-Long,Feng, Qiu,Wang, Huan,Lu, Jia-Xing
, p. 12216 - 12219 (2015)
A novel way to accommodate heterogeneous catalysis, CO2 fixation and asymmetric synthesis on one catalyst is reported. The [Co]@Ag composite was prepared for the first time and used for asymmetric carboxylation of benzyl bromides with CO2. All the procedures were performed under mild conditions. Moreover, the [Co]@Ag composite has terrific stability and reusability.
Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases
Zhang, Xiaotong,Bao, Ye,Huang, Ke,Barnett-Rundlett, Kimber L.,Armstrong, Daniel W.
, p. 495 - 513 (2010)
Dalbavancin is a new compound of the macrocyclic glycopeptide family. It was covalently linked to 5 lm silica particles using two different binding chemistries. Approximately 250 racemates including (a) heterocyclic compounds, (b) chiral acids, (c) chiral amines, (d) chiral alcohols, (e) chiral sulfoxides and sulfilimines, (f) amino acids and amino acid derivatives, and (g) other chiral compounds were tested on the two new chiral stationary phases (CSPs) using three different mobile phases. As dalbavancin is structurally related to teicoplanin, the same set of chiral compounds was screened on two commercially available teicoplanin CSPs for comparison. The dalbavancin CSPs were able to separate some enantiomers that were not separated by the teicoplanin CSPs and also showed improved separations for many racemates. However, there were other compounds only separated or better separated on teicoplanin CSPs. Therefore, the dalbavancin CSPs are complementary to the teicoplanin CSPs.
La1?xSrxFeO3 perovskite electrocatalysts for asymmetric electrocarboxylation of acetophenone with CO2
Yang, Li-Rong,Zhang, Jing-Jie,Zhao, Yi-Jun,Wang, Zhuo-Lin,Wang, Huan,Lu, Jia-Xing
, (2021/10/04)
The use of La1?xSrxFeO3 (x= 0, 0.1, 0.2, 0.3, 0.4 and 0.5) cathodes in asymmetric electrocarboxylation of acetophenone with CO2 induced by chiral auxiliary CoII-(salen) was investigated for the first time. Optically active 2-hydroxy-2-phenylpropionic acid with 94% enantiomeric excess and 68% yield were obtained. The superior asymmetric electrocarboxylation performance may derive from the Fe4+ species and the increased lattice oxygen concentration on the surface of La0.7Sr0.3FeO3 (LSF-0.3) induced by Sr-doping, together with an accelerated electron transfer and an increased electrochemically active surface area. Here, perovskite oxide catalyst has an acid function, which is supplied by Fe4+ ions, can participate in the reaction by coordinating with acetophenone. Moreover, the LSF-0.3 has considerable stability and reusability. By cyclic voltammograms and contrast experiments, a mechanism was proposed for the asymmetric electrocarboxylation reaction.
Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones
Keeri, Abdul Raheem,Gualandi, Andrea,Mazzanti, Andrea,Lewinski, Janusz,Cozzi, Pier Giorgio
supporting information, p. 18949 - 18952 (2016/01/26)
The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92 %), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.
An efficient synthetic approach towards fully functionalized tetronic acids: The use of 1,3-dioxolane-2,4-diones as novel protected-activated synthons of α-hydroxy acids
Prousis, Kyriakos C.,Markopoulos, John,Mckee, Vickie,Igglessi-Markopoulou, Olga
, p. 8637 - 8648 (2015/10/19)
A new strategy for the synthesis of tetronic acids with control over the regioselective introduction of substituents at the C-5 position has been developed. The construction of the densely functionalized quaternary carbon center within these molecules is of great importance. The key element for the proposed protocol was the utilization of O-carboxyanhydrides (OCA's) of optically active α-hydroxy acids, as promising bidentate protective/activating precursors. The structure of the new compounds was investigated by using NMR spectral data and X-ray structural analyses.
Absolute configuration and enantiomeric composition of partially resolved mandelic,atrolactic and lactic acids by 1H NMR of their (S)-2-methylbutyl esters
Da C. Andrade, Francisco A.,De L. Mendes, Maricleide P.,Da Fonseca, Neuracy C.
, p. 1006 - 1011 (2013/08/23)
The mandelic,atrolactic and lactic acid esters of the (S)-2-methyl-1- butanol were examined as diastereomeric derivatives for the stereochemical analysis of the mentioned acids by 1H nuclear magnetic resonance (NMR) at 300 MHz. The diastereomer
Enantioselective synthesis of either enantiomer of α-alkyl-α- hydroxy-α-phenylacetic acids using chiral auxiliaries
Perez-Estrada, Salvador,Lagunas-Rivera, Selene,Vargas-Diaz, Maria Elena,Velazquez-Ponce, Pedro,Joseph-Nathan, Pedro,Zepeda, L. Gerardo
, p. 1837 - 1843 (2007/10/03)
The enantioselective synthesis of either enantiomer of α-alkyl- α-hydroxy-α-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee).
