ChemInform Abstract: Highly Enantioselective Biginelli Reaction Promoted by Chiral Bifunctional Primary Amine-Thiourea Catalysts: Asymmetric Synthesis of Dihydropyrimidines.

ChemInform ◽  
2010 ◽  
Vol 41 (18) ◽  
Author(s):  
Yangyun Wang ◽  
Haitao Yang ◽  
Jipan Yu ◽  
Zhiwei Miao ◽  
Ruyu Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Primary Amine ◽  
Biginelli Reaction

Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Science ◽  
2018 ◽  
Vol 360 (6396) ◽  
pp. 1438-1442 ◽  
Author(s):  
Jianfeng Chen ◽  
Xing Gong ◽  
Jianyu Li ◽  
Yingkun Li ◽  
Jiguo Ma ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
High Activity ◽  
Asymmetric Catalysis ◽  
Carbonyl Group ◽  
Mannich Reaction ◽  
Primary Amine ◽  
Chiral Amines ◽  
Carbonyl Groups ◽  
Diphenylphosphinyl Imines

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Stereoselectivity of the Biginelli Reaction Catalyzed by Chiral Primary Amine: A Computational Study

Heterocycles ◽  
2021 ◽  
Vol 103 (2) ◽  
pp. 893
Author(s):  
Miho Hatanaka ◽  
Takayoshi Yoshimura ◽  
Maneeporn Puripat ◽  
Vudhichai Parasuk
Keyword(s):  
Primary Amine ◽  
Computational Study ◽  
Biginelli Reaction

scholarly journals Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3902
Author(s):  
Mei Kee Kam ◽  
Akira Sugiyama ◽  
Ryouta Kawanishi ◽  
Kazutaka Shibatomi
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Substitution ◽  
Primary Amine ◽  
Tetrabutylammonium Hydroxide ◽  
Tertiary Alcohols ◽  
Tertiary Carbon ◽  
Chiral Tertiary Alcohols

Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.

Cooperative and Enantioselective NbCl5/Primary Amine Catalyzed Biginelli Reaction

2010 ◽  
Vol 2010 (26) ◽  
pp. 4986-4990 ◽  
Author(s):  
Yong-Feng Cai ◽  
Hua-Meng Yang ◽  
Li Li ◽  
Ke-Zhi Jiang ◽  
Guo-Qiao Lai ◽  
...  
Keyword(s):  
Primary Amine ◽  
Biginelli Reaction
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