Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis

ChemInform ◽  
2003 ◽  
Vol 34 (44) ◽  
Author(s):  
Stefan France ◽  
David J. Guerin ◽  
Scott J. Miller ◽  
Thomas Lectka
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amines

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.

ChemInform Abstract: Asymmetric Synthesis of Substituted NH-Piperidines from Chiral Amines.

ChemInform ◽  
2015 ◽  
Vol 46 (4) ◽  
pp. no-no
Author(s):  
Lekh Nath Gautam ◽  
Yijin Su ◽  
Novruz G. Akhmedov ◽  
Jeffrey L. Petersen ◽  
Xiaodong Shi
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amines

Asymmetric synthesis of substituted NH-piperidines from chiral amines

2014 ◽  
Vol 12 (33) ◽  
pp. 6384-6388 ◽  
Author(s):  
Lekh Nath Gautam ◽  
Yijin Su ◽  
Novruz G. Akhmedov ◽  
Jeffrey L. Petersen ◽  
Xiaodong Shi
Keyword(s):  
Asymmetric Synthesis ◽  
Condensation Reaction ◽  
Chiral Amines

Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction.

An Advance on ExploringN-tert-Butanesulfinyl Imines in Asymmetric Synthesis of Chiral Amines

2008 ◽  
Vol 41 (7) ◽  
pp. 831-840 ◽  
Author(s):  
Guo-Qiang Lin ◽  
Ming-Hua Xu ◽  
Yu-Wu Zhong ◽  
Xing-Wen Sun
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Amines
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