Effect of Methyl-substitution of the Quinoline Ring of Cinchona Alkaloids on the Performance as a Modifier for the Enantioselective Hydrogenation of (E)-2,3-di(4-methoxyphenyl)propenoic Acid Over Pd/C: Kinetic Analysis

2020 ◽  
Author(s):  
Makoto Nakatsuji ◽  
Takeshi Kubota ◽  
Morifumi Fujita ◽  
Yasuaki Okamoto ◽  
Takashi Sugimura
Keyword(s):  
Kinetic Analysis ◽  
Enantioselective Hydrogenation ◽  
Cinchona Alkaloids ◽  
Quinoline Ring ◽  
Methyl Substitution ◽  
Propenoic Acid

Kinetic analysis of the asymmetric hydrogenation of (E)-2,3-diphenylpropenoic acid over cinchonidine derivative-modified Pd/C: quinoline ring modification

2020 ◽  
Vol 10 (19) ◽  
pp. 6573-6582
Author(s):  
Makoto Nakatsuji ◽  
Morifumi Fujita ◽  
Yasuaki Okamoto ◽  
Takashi Sugimura
Keyword(s):  
Kinetic Analysis ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Quinoline Ring

The substitutions at the 2′- and/or 6′-positions of the quinoline ring of cinchonidine reduce both the intrinsic enantioselectivity and adsorption strength for the enantioselective hydrogenation of α-phenylcinnamic acid over Pd/C.

Kinetic Analysis of Enantioselective Hydrogenation of 2,3-(E)-Diarylpropenoic Acids over a Chiral Cinchona Alkaloid-Modified Pd/C Catalyst

2020 ◽  
Vol 93 (1) ◽  
pp. 163-175 ◽  
Author(s):  
Bokeun Kim ◽  
Makoto Nakatsuji ◽  
Takuya Mameda ◽  
Takeshi Kubota ◽  
Morifumi Fujita ◽  
...  
Keyword(s):  
Kinetic Analysis ◽  
Enantioselective Hydrogenation ◽  
Cinchona Alkaloid

scholarly journals Vibrational Spectroscopic Study of the Cocrystal Products Formed by Cinchona Alkaloids with 5-Nitrobarbituric Acid

2015 ◽  
Vol 2015 ◽  
pp. 1-13 ◽  
Author(s):  
Harry G. Brittain
Keyword(s):  
Differential Scanning Calorimetry ◽  
Molecular Complexes ◽  
Ring System ◽  
Cinchona Alkaloids ◽  
Infrared Absorption Spectroscopy ◽  
Quinoline Ring ◽  
Scanning Calorimetry ◽  
X Ray ◽  
Structural Types ◽  
Chemical Microscopy

X-ray powder diffraction, differential scanning calorimetry, infrared absorption spectroscopy, and Raman spectroscopy have been used to study the phenomenon of cocrystal formation in the molecular complexes formed by 5-nitrobarbituric acid with four cinchona alkaloids. The cocrystal products were found to contain varying degrees of hydration, ranging from no hydration in the nitrobarbiturate-quinidine cocrystal up to a 4.5-hydrate species in the nitrobarbiturate-cinchonine cocrystal. For the nitrobarbiturate cocrystals with cinchonine, cinchonidine, and quinidine, the predominant interaction was with the quinoline ring system of the alkaloid. However, for quinine, the predominant interaction was with the quinuclidine group of the alkaloid. These properties serve to demonstrate the utility of 5-nitrobarbituric acid as a preferred reagent for chemical microscopy, since the differing range of hydrate and structural types would serve to easily differentiate the cinchona alkaloids from each other, even when different compounds contained the same absolute configurations at their dissymmetric centers.

Article

1998 ◽  
Vol 76 (9) ◽  
pp. 1304-1307
Author(s):  
Yoshifumi Yuasa ◽  
Yoko Yuasa ◽  
Haruki Tsuruta
Keyword(s):  
Building Block ◽  
Enantioselective Hydrogenation ◽  
Renin Inhibitor ◽  
Renin Inhibitors ◽  
Propenoic Acid ◽  
Chiral Building Block

(2S)-3-(tert-Butylsulfonyl)-2-benzylpropionic acid 1, which is used as the N-terminal chiral building block of renin inhibitors, is synthesized from (Z)-2-(tert-butylsulfonylmethyl)-3-phenyl-2-propenoic acid 6 by enantioselective hydrogenation using Ru-BINAP complexes in the presence of triethylamine with 84% ee. The enantioselective hydrogenation of a substrate with sulfone functionality is first reported.Key words: hydrogenation, enantioselectivity, Ru-BINAP, oxidation, renin inhibitor.

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