Asymmetric Synthesis of N-(Diphenylphosphinyl)amines Promoted by Chiral Carbosilane Dendritic Ligands in The Enantioselective Addition of Dialkylzinc Compounds to N-(Diphenylphosphinyl)imines

2002 ◽  
Vol 2002 (18) ◽  
pp. 3115-3118 ◽  
Author(s):  
Itaru Sato ◽  
Kenji Hosoi ◽  
Ryo Kodaka ◽  
Kenso Soai
Keyword(s):  
Asymmetric Synthesis ◽  
Enantioselective Addition ◽  
Diphenylphosphinyl Imines

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.

scholarly journals Asymmetric synthesis with "privileged" ligands

2001 ◽  
Vol 73 (2) ◽  
pp. 325-329 ◽  
Author(s):  
Marco Bandini ◽  
Pier Giorgio Cozzi ◽  
Achille Umani-Ronchi
Keyword(s):  
Open Access ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Aromatic Aldehydes ◽  
Redox Processes ◽  
Asymmetric Allylation ◽  
Salen Complexes ◽  
Allyl Halides ◽  
Different Types ◽  
Enantioselective Addition

Different types of chiral "privileged" ligands 1 and 2 in promoting enantioselective addition of allylating agents to aliphatic and aromatic aldehydes are described. Here, a new concept in the asymmetric allylation reaction is presented. Redox [Cr (Salen) ] mediated addition of allyl halides to carbonyl compounds is described, and mechanistic investigations are discussed. These results open access to the fascinating area of the catalytic redox processes mediated by metallo-Salen complexes.

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