Asymmetric Michael Reaction of Malonate Derivatives with α,β-Unsaturated Ketones Using Chiral Quaternary Ammonium Salts.

ChemInform ◽  
2006 ◽  
Vol 37 (52) ◽  
Author(s):  
Min Je Cho ◽  
Myoung Gi Cho ◽  
Sun Chul Huh ◽  
Sung Min Kim ◽  
Kilsung Lee ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Michael Reaction ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Unsaturated Ketones ◽  
Asymmetric Michael Reaction

scholarly journals A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water

2021 ◽  
Vol 2021 ◽  
pp. 1-10
Author(s):  
Alemayehu Mekonnen ◽  
Alemu Tesfaye
Keyword(s):  
Quaternary Ammonium ◽  
Phase Transfer ◽  
Conjugate Addition ◽  
Quaternary Ammonium Salts ◽  
Cinchona Alkaloids ◽  
Ammonium Salts ◽  
Alkylation Reaction ◽  
Pt Catalysts ◽  
Unsaturated Ketones ◽  
Catalytic Performances

Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%–96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.

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