Enantioselective transfer hydrogenation, a key step for the synthesis of 3-aminotetrahydroquinolines

2016 ◽  
Vol 40 (11) ◽  
pp. 9034-9037 ◽  
Author(s):  
Alexandre Aillerie ◽  
Vincent Lemau de Talencé ◽  
Clément Dumont ◽  
Sylvain Pellegrini ◽  
Frédéric Capet ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Catalytic Amount ◽  
Transfer Hydrogenation ◽  
Mild Conditions ◽  
Chiral Phosphoric Acid

An enantioselective transfer hydrogenation has been successfully achieved to furnish 3-aminotetrahydroquinolines. The reaction was conducted in the presence of Hantzsch dihydropyridine and a catalytic amount of chiral phosphoric acid under mild conditions.

scholarly journals Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingguang Li ◽  
Meng Duan ◽  
Peiyuan Yu ◽  
K. N. Houk ◽  
Jianwei Sun
Keyword(s):  
Hydrogen Bonding ◽  
Phosphoric Acid ◽  
Nucleophilic Addition ◽  
Acid Catalysis ◽  
Conjugate Addition ◽  
Mild Conditions ◽  
Rapid Construction ◽  
Chiral Phosphoric Acid ◽  
Cyclic Molecules ◽  
Selectivity Control

AbstractCatalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.

Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of 3-trifluoromethylthioquinolines

2016 ◽  
Vol 14 (29) ◽  
pp. 6937-6941 ◽  
Author(s):  
Ji Zhou ◽  
Qian-Fan Zhang ◽  
Wei-Hao Zhao ◽  
Guo-Fang Jiang
Keyword(s):  
Phosphoric Acid ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

A chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of 3-trifluoromethylthioquinolines was developed, providing chiral 2,3-disubstituted 1,2,3,4-tetrahydroquinoline derivatives containing a stereogenic trifluoromethylthio group with up to 99% enantioselectivity.

ChemInform Abstract: Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Hydrogenation of ortho-Hydroxyaryl Alkyl N-H Ketimines.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Thanh Binh Nguyen ◽  
Hadjira Bousserouel ◽  
Qian Wang ◽  
Francoise Gueritte
Keyword(s):  
Phosphoric Acid ◽  
Transfer Hydrogenation ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of quinazolinones

2019 ◽  
Vol 60 (33) ◽  
pp. 150947
Author(s):  
Fan-Jie Meng ◽  
Lei Shi ◽  
Wen-Feng Jiang ◽  
Guang-Shou Feng ◽  
Xiao-Bing Lu ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed
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