179601-87-7Relevant academic research and scientific papers
Determination of absolute configuration of trans-2-arylcyclohexanols using remarkable aryl-induced 1H NMR shifts in diastereomeric derivatives
Matsugi, Masato,Itoh, Kinuyo,Nojima, Masatomo,Hagimoto, Yuri,Kita, Yasuyuki
, p. 6903 - 6905 (2001)
A facile determination of the absolute configuration of trans-2-arylcyclohexanols was achieved. It takes advantage of the observations of the remarkable aryl-induced 1H NMR shifts that seems to be ascribable to the discrimination of the diastereo-environment between intermediary optically active diastereomers by intramolecular CH/π interaction.
Synthesis method of chiral trans-2-substituted naphthenic alcohol
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Paragraph 0041-0045; 0050-0051, (2021/09/08)
The invention relates to a synthesis method of chiral trans-2-substituted naphthenic alcohol. The invention provides a method for synthesizing chiral trans-cycloalkanol through asymmetric hydrogenation of palladium-catalyzed 2-substituted cyclic ketone. According to the method,a chiral diphosphine P-P * complex of metal palladium is taken as a catalyst, an acid additive is used in cooperation, asymmetric hydrogenation is carried out on a 2-substituted cyclic ketone compound to obtain a corresponding chiral trans-cycloalkanol compound. the enantiomeric excess of the chiral trans-cycloalkanol compound can reach 97% at most, and the trans-selectivity of the chiral trans-cycloalkanol compound is up to 20: 1. The method is simple and convenient to operate, practical, easy to implement, high in yield, high in atom economy and environment-friendly; the catalyst is commercially available; the reaction conditions are mild; and the method has a potential practical application value.
Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis oftranscycloalkanols through dynamic kinetic resolution under acidic conditions
Li, Xiang,Zhao, Zi-Biao,Chen, Mu-Wang,Wu, Bo,Wang, Han,Yu, Chang-Bin,Zhou, Yong-Gui
supporting information, p. 5815 - 5818 (2020/06/03)
The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiraltranscycloalkanol derivatives with excellent enantioselectivities.
Diastereoselective and enantioselective alkaline-hydrolysis of 2-aryl-1-cyclohexyl acetate: a CAL-B catalyzed deacylation/acylation tandem process
Belkacemi, Fatma Zahra,Merabet-Khelassi, Mounia,Aribi-Zouioueche, Louisa,Riant, Olivier
supporting information, p. 1644 - 1650 (2017/10/12)
Candida antarctica lipase proved to be a particularly efficient lipase for the resolution of racemic 2-arylcyclohexyl acetate in hydrolysis reaction with Na2CO3 in an organic medium. The (1R,2S)-trans-2-arylcyclohexanols 2a–2d were obtained with high ee values (up to >99%) and the selectivity reached E > 200. The influence of the enol ester and the solvent on (±)-trans-2-arylcyclohexanol in the CAL-B catalyzed acylation was also studied and compared with the deacylation. The CAL-B exhibits a better affinity for the alkaline hydrolysis reaction compared with acylation with the enol esters in the same organic solvents. The best conditions were applied to resolve a stereoisomeric mixture cis/trans-2-phenyl-1-cyclohexanol and its corresponding acetate by acylation and deacylation. The obtained results show a highly enantio- and diastereoselectivity of the CAL-B during the acylation and the deacylation in favor of the trans-(R)-enantiomer product. The resolution of a mixture of cis/trans-2-arylcyclohexanols was an easy, convenient approach to provide only one stereoisomer of a mixture of four with high enantiomeric excess.
A nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols via esterification using polymer-supported DCC, DMAP, and 3 β- acetoxyetienic acid
Shamoto, Kengo,Miyazaki, Atsushi,Matsukura, Mika,Kobayashi, Yuki,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 1425 - 1431 (2013/05/22)
A nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols was carried out by esterification using polymer-supported N,N′- dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP), and 3β-acetoxyetienic acid. The efficiency of the kinetic resolution was comparable to the enzymatic method when arylcyclohexanols bearing a condensed-aromatic ring were used. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communication to view the free supplemental file.
Organolithium/chiral Lewis base/BF3: A versatile combination for the enantioselective desymmetrization of meso-epoxides
Vrancken, Emmanuel,Alexakis, Alexandre,Mangeney, Pierre
, p. 1354 - 1366 (2007/10/03)
BF3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring-opening or the carbenoidic rearrangement of various meso-oxiranes with excellent yields and ee values of up to 87%. Mechanistic aspects of these reactions are considered. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Effective nonenzymatic kinetic resolution of (±)-trans-2-arylcyclohexanols using 3β-acetoxyetienic acid, DCC, and DMAP
Matsugi, Masato,Hagimoto, Yuri,Nojima, Masatomo,Kita, Yasuyuki
, p. 583 - 584 (2013/09/05)
(1R,2S)-trans-2-Arylcyclohexanols of high enantiomerically purity were obtained by the simple stirring of the corresponding (±)-arylcyclohexanols with 3β-acetoxyetienic acid, DCC, and DMAP at room temperature.
