Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis

2010 ◽  
Vol 132 (20) ◽  
pp. 7216-7228 ◽  
Author(s):  
Shenshen Hu ◽  
Jiuyuan Li ◽  
Junfeng Xiang ◽  
Jie Pan ◽  
Sanzhong Luo ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Primary Amine ◽  
Selective Recognition ◽  
Aqueous Buffer ◽  
Amine Catalysis

Expanding the Scope of Primary Amine Catalysis: Stereoselective Synthesis of Indanedione-Fused 2,6-Disubstituted trans-Spirocyclohexanones

2016 ◽  
Vol 81 (6) ◽  
pp. 2420-2431 ◽  
Author(s):  
G. Madhusudhan Reddy ◽  
Chi-Ting Ko ◽  
Kai-Hong Hsieh ◽  
Chia-Jui Lee ◽  
Utpal Das ◽  
...  
Keyword(s):  
Primary Amine ◽  
Stereoselective Synthesis ◽  
Amine Catalysis

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.

Chiral Primary Amine Catalysis for Asymmetric Mannich Reactions of Aldehydes with Ketimines: Stereoselectivity and Reactivity

2017 ◽  
Vol 56 (41) ◽  
pp. 12697-12701 ◽  
Author(s):  
Jun Dai ◽  
Dan Xiong ◽  
Tengrui Yuan ◽  
Juan Liu ◽  
Tao Chen ◽  
...  
Keyword(s):  
Primary Amine ◽  
Mannich Reactions ◽  
Amine Catalysis

Asymmetric Retro-Claisen Reaction by Chiral Primary Amine Catalysis

2016 ◽  
Vol 138 (12) ◽  
pp. 3978-3981 ◽  
Author(s):  
Yunbo Zhu ◽  
Long Zhang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Amine Catalysis ◽  
Claisen Reaction

Chiral Primary Amine Catalysis for Asymmetric Mannich Reactions of Aldehydes with Ketimines: Stereoselectivity and Reactivity

2017 ◽  
Vol 129 (41) ◽  
pp. 12871-12875 ◽  
Author(s):  
Jun Dai ◽  
Dan Xiong ◽  
Tengrui Yuan ◽  
Juan Liu ◽  
Tao Chen ◽  
...  
Keyword(s):  
Primary Amine ◽  
Mannich Reactions ◽  
Amine Catalysis

Primary amine catalysis of the cleavage of mesityl oxide to acetone

1972 ◽  
Vol 94 (7) ◽  
pp. 2534-2535
Author(s):  
Ralph M. Pollack ◽  
David Strohbeen
Keyword(s):  
Primary Amine ◽  
Mesityl Oxide ◽  
Amine Catalysis

scholarly journals (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

2016 ◽  
Vol 12 ◽  
pp. 462-495 ◽  
Author(s):  
Giorgos Koutoulogenis ◽  
Nikolaos Kaplaneris ◽  
Christoforos G Kokotos
Keyword(s):  
Asymmetric Catalysis ◽  
Secondary Amine ◽  
Tertiary Amine ◽  
Primary Amine ◽  
Membered Ring ◽  
Chiral Centers ◽  
Synthetic Chemist ◽  
Functionalization Reaction

Organocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas will be summarized. Initially, the use of primary amine-thioureas as organocatalysts for the above transformation is being discussed, followed by the examples employing secondary amine-thioureas. Finally, the use of tertiary amine-thioureas and miscellaneous examples are presented.

Photoredox Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis

Synthesis ◽  
2021 ◽  
Author(s):  
Zongbin Jia ◽  
Qi Yang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Tertiary Amines ◽  
Dehydrogenative Coupling ◽  
Cross Coupling Reaction ◽  
Iminium Ion ◽  
Amine Catalysis ◽  
Catalytic Asymmetric

We report herein a catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, following by isomerization, leading to aza-Morita-Baylis-Hillman-type products with good diastereo- and enantio- selectivity.

ChemInform Abstract: Asymmetric Retro-Claisen Reaction by Chiral Primary Amine Catalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (37) ◽  
Author(s):  
Yunbo Zhu ◽  
Long Zhang ◽  
Sanzhong Luo
Keyword(s):  
Primary Amine ◽  
Amine Catalysis ◽  
Claisen Reaction
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