377775-90-1Relevant academic research and scientific papers
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.
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.
1H NMR determination of absolute configuration of 1- or 2-aryl-substituted alcohols and amines by means of their diastereomers: Novel separation technique of diastereomeric derivatives of pyridyl alcohols by extraction
Matsugi, Masato,Itoh, Kinuyo,Nojima, Masatomo,Hagimoto, Yuri,Kita, Yasuyuki
, p. 5551 - 5564 (2007/10/03)
Abstract: A convenient method to determine the absolute configuration of trans-2-aryl cyclohexanols, 1-aryl alcohols and amines was achieved. This method takes advantage of the 1H NMR spectroscopic observations of the remarkable high-field shift of C18-CH3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3β-acetoxy-5-etienic acid. Furthermore, it was observed that the corresponding diastereomeric derivatives of the pyridyl alcohols were simply separated by extraction based on the difference in their basicity.
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 (2007/10/03)
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.
