Direct Asymmetric Michael Reaction of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Two Secondary Amine Catalysts

2018 ◽  
Vol 130 (7) ◽  
pp. 1976-1980 ◽  
Author(s):  
Yujiro Hayashi ◽  
Nariyoshi Umekubo
Keyword(s):  
Secondary Amine ◽  
Michael Reaction ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones ◽  
Asymmetric Michael Reaction ◽  
Amine Catalysts

scholarly journals Evidence for an enolate mechanism in the asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones via a hybrid system of two secondary amine catalysts

2020 ◽  
Vol 11 (41) ◽  
pp. 11293-11297 ◽  
Author(s):  
Nariyoshi Umekubo ◽  
Takahiro Terunuma ◽  
Eunsang Kwon ◽  
Yujiro Hayashi
Keyword(s):  
Hybrid System ◽  
Secondary Amine ◽  
Michael Reaction ◽  
Silyl Ether ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones ◽  
Asymmetric Michael Reaction ◽  
Amine Catalysts

The key nucleophile was found to be neither an enamine nor an enol, but an enolate in the direct Michael reaction of α,β-unsaturated aldehydes and non-activated ketones catalyzed by two amine catalysts namely diphenylprolinol silyl ether and pyrrolidine.

Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes

2016 ◽  
Vol 14 (16) ◽  
pp. 3926-3933 ◽  
Author(s):  
Shanchao Wu ◽  
Yu Li ◽  
Yongqiang Zhang ◽  
Kun Fang ◽  
Guoqiang Dong ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Michael Addition ◽  
Michael Reaction ◽  
Catalytic Amount ◽  
Unsaturated Aldehydes ◽  
The Michael Reaction

The Michael reaction of substituted isorhodanines with α,β-unsaturated aldehydes in the presence of a catalytic amount of a chiral secondary amine is presented.

Regio-, Stereo- and Enantioselective α-Addition of Carbonyl Nucleo-philes to Allenamides Catalyzed by a Synergistic Copper/Enamine System

2020 ◽  
Author(s):  
Rémi Blieck ◽  
Sebastien Lemouzy ◽  
Marc Taillefer ◽  
Florian Monnier
Keyword(s):  
Catalytic System ◽  
Secondary Amine ◽  
Primary Amine ◽  
Synergistic Catalysis ◽  
Enantioselective Addition ◽  
Amine Catalysts

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

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