Unusual Diastereofacial Selectivity in the Michael Addition Reactions of Lithiated 2-Aminoacetates and -acetamides to α,β-Unsaturated Carbonyl Compounds

1992 ◽  
Vol 21 (9) ◽  
pp. 1801-1804 ◽  
Author(s):  
Shuji Kanemasa ◽  
Masafumi Nomura ◽  
Yasuhisa Taguchi
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Addition Reactions ◽  
The Michael Addition

Theoretical studies on the activation mechanism involving bifunctional tertiary amine–thioureas and isatylidene malononitriles

RSC Advances ◽  
2015 ◽  
Vol 5 (43) ◽  
pp. 34314-34318 ◽  
Author(s):  
Zheng-Hang Qi ◽  
Ye Zhang ◽  
Gui-Yu Ruan ◽  
Yi Zhang ◽  
Yong Wang ◽  
...  
Keyword(s):  
Tertiary Amine ◽  
Michael Addition ◽  
Activation Mechanism ◽  
Addition Reactions ◽  
Theoretical Studies ◽  
Dft Studies ◽  
The Michael Addition

DFT studies on the activation mechanism of the Michael addition reactions containing bifunctional tertiary amine–thioureas and isatylidene malononitriles have been performed at the B3LYP/6-311++G(d,p)//B3LYP/6-31G(d) level of theory.

Curve crossing analysis of LFER data in Michael addition reactions

1992 ◽  
Vol 70 (4) ◽  
pp. 1022-1027 ◽  
Author(s):  
Zeev Gross ◽  
Shmaryahu Hoz
Keyword(s):  
Chemical Shift ◽  
Transition State ◽  
Michael Addition ◽  
Electronic Configuration ◽  
Nucleophilic Attack ◽  
Addition Reactions ◽  
Rate Correlation ◽  
The Michael Addition ◽  
Curve Crossing

Rate constants for the Michael addition of CN− in water, aqueous sulfolane, and DMSO, and MeO− in MeOH to eight mono- and disubstituted 1,1-diaryl-2,2-dinitroethylenes were measured. The ρ values are in the range 0.7 (CN−/H2O) –1.6 (MeO−/MeOH). For each of the four systems a correlation was found between log k and the 13C chemical shift of the carbon that undergoes the nucleophilic attack. However, the quality of the correlation as well as the slope decreases with decreasing ρ values. Analysis of the electronic configuration of the transition state using the curve crossing model shows that the traditional interpretation of the location of the transition state should be reversed. This analysis provides a rationale for the observed dependence of the chemical shift – rate correlation on the ρ value.

Carcinogenicity of lactones. IV. Alkylation of analogues of DNA guanine groups such as imidazole, N-methylimidazole, and guanosine by α, β-unsaturated acids

1970 ◽  
Vol 48 (10) ◽  
pp. 1566-1573 ◽  
Author(s):  
J. Bryan Jones ◽  
John M. Young
Keyword(s):  
Michael Addition ◽  
Alkylating Agents ◽  
Addition Reactions ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
The Michael Addition

Studies on the reactions of carcinogenic γ-lactones and related compounds with analogues of guanine DNA residues indicate that the lactones themselves will not effect permanent alkylation of the guanine N-7 position since the Michael addition reactions involved would be readily reversible. In contrast, the α,β-unsaturated acids resulting from hydrolysis of such lactones are effective guanine N-7 alkylating agents owing to zwitterionic stabilization of the corresponding Michael addition products.

Preparation of a chiral Pt12 tetrahedral cage and its use in catalytic Michael addition reaction

2018 ◽  
Vol 54 (38) ◽  
pp. 4814-4817 ◽  
Author(s):  
Imtiyaz Ahmad Bhat ◽  
Anthonisamy Devaraj ◽  
Prodip Howlader ◽  
Ki-Whan Chi ◽  
Partha Sarathi Mukherjee
Keyword(s):  
Michael Addition ◽  
Self Assembly ◽  
Addition Reaction ◽  
Addition Reactions ◽  
Stoichiometric Ratio ◽  
Michael Addition Reaction ◽  
Methanol Mixture ◽  
Hexadentate Ligand ◽  
The Michael Addition

A chiral M12L4 molecular tetrahedron (T) was synthesized by self-assembly of chiral cis-[(1S,2S)-dch]Pt(NO3)2 (M) with a hexadentate ligand (L) in 3 : 1 stoichiometric ratio. The cage T was found to catalyze the Michael addition reactions of series of nitrostyrene derivatives with indole in (9 : 1) water–methanol mixture.

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