scholarly journals New L-Serine Derivative Ligands as Cocatalysts for Diels-Alder Reaction

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Carlos A. D. Sousa ◽  
José E. Rodríguez-Borges ◽  
Cristina Freire
Keyword(s):  
Catalytic Activity ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reaction Yield ◽  
Catalytic Potential ◽  
Diels Alder Reaction ◽  
Good Ability ◽  
Medium Strength

New L-serine derivative ligands were prepared and tested as cocatalyst in the Diels-Alder reactions between cyclopentadiene (CPD) and methyl acrylate, in the presence of several Lewis acids. The catalytic potential of the in situ formed complexes was evaluated based on the reaction yield. Bidentate serine ligands showed good ability to coordinate medium strength Lewis acids, thus boosting their catalytic activity. The synthesis of the L-serine ligands proved to be highly efficient and straightforward.

scholarly journals Ionic liquids - deanol derivatives as the Diels-Alder reaction solvents

2010 ◽  
Vol 8 (5) ◽  
pp. 1140-1146 ◽  
Author(s):  
Ewa Janus ◽  
Anna Syguda ◽  
Katarzyna Materna
Keyword(s):  
Catalytic Activity ◽  
Ionic Liquids ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reaction Yield ◽  
Catalytic Systems ◽  
Diels Alder Reaction ◽  
Lewis Acid Catalyst ◽  
Metal Triflates

AbstractThe Diels-Alder reaction between cyclopentadiene and dienophiles in deanol derivatives containing bis(trifluoromethylsulfonyl)imide anion as media have been studied. The effect of the substituents attached to the cation on the endo:exo selectivity as well as the reaction yield have been evaluated in the absence and presence of Lewis acid catalyst - Y(OTf)3. Catalytic activity of metal triflates and the recycling of chosen catalytic systems have also been investigated

Influence of Lewis Acids on the Diels–Alder Reaction. IV. Reaction of 2-Methyl- and 2-Phenylfuran with Ethyl Propiolate

1971 ◽  
Vol 49 (19) ◽  
pp. 3152-3157 ◽  
Author(s):  
A. W. Mcculloch ◽  
A. G. McInnes
Keyword(s):  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Methyl Propionate ◽  
Diels Alder Reaction ◽  
By Products

The AlCl3-promoted reactions of 2-methyl- and of 2-phenylfuran with ethyl propiolate afford as major products ethyl 5-hydroxy-2-methyl- and 2-phenylbenzoates (6a, 6b). Also isolated as minor by-products of these reactions are ethyl 3-(2-furyl-5-methyl)acrylate (5a), ethyl 3-(2-furyl-5-phenyl)acrylate (5b), ethyl 3,3-di(2-furyl-5-methyl)propionate (10a), ethyl 3,3-di(2-furyl-5-phenyl)propionate (10b), and ethyl 2-hydroxy-5-methylbenzoate (8a).

Organocatalytic enantioselective Diels–Alder reaction between hydroxymaleimides and in situ generated nitrosoalkenes for direct preparation of chiral hemiketals with 1,2-oxazine skeleton

2021 ◽  
Author(s):  
Min Xiang ◽  
Chen-Yi Li ◽  
Jian Zhang ◽  
Ying Zou ◽  
Wen-Sheng Li ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Direct Preparation

Organocatalytic Enantioselective IEDDA reaction between hydroxymaleimides and in situ generated nitrosoalkenes has been disclosed, a series of chiral hemiketals containing 5,6-dihydro-4H-l,2-oxazines and succinimide frameworks have been prepared.

scholarly journals Borenium ionic liquids as catalysts for Diels–Alder reaction: tuneable Lewis superacids for catalytic applications

2017 ◽  
Vol 7 (5) ◽  
pp. 1045-1049 ◽  
Author(s):  
K. Matuszek ◽  
S. Coffie ◽  
A. Chrobok ◽  
M. Swadźba-Kwaśny
Keyword(s):  
Catalytic Activity ◽  
Ionic Liquids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Lewis Acidity ◽  
High Catalytic Activity ◽  
Acceptor Number ◽  
Diels Alder Reaction ◽  
Catalytic Applications

Ionic liquids with Lewis superacidic borenium cations were used as catalysts in solvent-less Diels–Alder cycloaddition. The extremely high catalytic activity correlated with the Lewis acidity, expressed as the Gutmann acceptor number.

An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions

2006 ◽  
Vol 84 (10) ◽  
pp. 1487-1503 ◽  
Author(s):  
Douglas P Heller ◽  
Daniel R Goldberg ◽  
Hongqiao Wu ◽  
William D Wulff
Keyword(s):  
Asymmetric Catalysis ◽  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Catalytic ◽  
Diels Alder Reaction ◽  
Positive Cooperativity ◽  
Derivatives Of ◽  
Methyl Phenyl

Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-di-t-butylphenyl. All of these ligands give lower asymmetric inductions than the unsubstituted VAPOL for the Diels–Alder reactions of both methyl acrylate and methacrolein. The positive cooperativity of added carbonyl compounds on the autoinduction in the Diels–Alder reaction of methyl acrylate and cyclopentadiene were also investigated with the VANOL and VAPOL ligands as well as the 6,6′-dibromo and 6,6′-diphenyl derivatives of VAPOL. Only the reaction with VAPOL showed any significant positive cooperativity. The reaction with VANOL was sluggish at –78 °C, but at higher temperatures, the reaction did exhibit positive cooperativity that was similar to that of VAPOL. Finally, no positive cooperativity was observed with the VAPOL ligand for the reaction of methacrolein and cyclopentadiene.Key words: Diels–Alder, asymmetric catalysis, vaulted biaryl ligands, VANOL, VAPOL.

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