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.

Efficient Enantioselective Michael Addition of Nitroalkenes Catalyzed by a New Surfactant-Type Thiourea Organocatalyst in Water

2014 ◽  
Vol 1015 ◽  
pp. 602-605 ◽  
Author(s):  
Hong Ying Zhang ◽  
Xue Ming Yan
Keyword(s):  
Michael Addition ◽  
Room Temperature ◽  
Michael Reaction ◽  
The Michael Reaction

A new surfactant-type bifunctional thiourea organocatalysts were synthesized. In the presence of 10 mol% PhCOOH, the Michael reaction of nitroalkenes with various nucleophiles could be catalyzed smoothly by this new organocatalyst in water at room temperature, giving the desired adducts in good yields with high diastereoselectivities (syn/anti=82/18->99/1) and excellent enantioselectivities (up to 97% ee)

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.

Sterically hindered 1,3-diketones in the Michael reaction

1996 ◽  
Vol 45 (1) ◽  
pp. 137-139
Author(s):  
I. E. Sokolov ◽  
A. S. Zanina ◽  
S. I. Shergina ◽  
M. S. Shvartsberg
Keyword(s):  
Michael Reaction ◽  
Sterically Hindered ◽  
The Michael Reaction
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