ChemInform Abstract: Substituted 1-Thia-3-aza-1,3-butadiene: Diels-Alder Reaction with Methyl Acrylate. Determination of Activation Parameters.

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).

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The RHF– and UHF–AM1 potential-energy surfaces for the diels–alder reaction of substituted butadienes with substituted ethenes. Part 58.—Determination of reactivity by MO theory

Journal of the Chemical Society Faraday Transactions 2 Molecular and Chemical Physics ◽

10.1039/f29898500867 ◽

1989 ◽

Vol 85 (7) ◽

pp. 867-877 ◽

Cited By ~ 8

Author(s):

Jae Young Choi ◽

Ikchoon Lee

Keyword(s):

Potential Energy ◽

Potential Energy Surfaces ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Energy Surfaces ◽

Mo Theory

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ChemInform Abstract: Hetero-Diels-Alder Reaction of Substituted 1-Oxabutadienes and 2-Ethoxyvinyl Acetate. An Entry to Various Natural Occurring Carbohydrates.

ChemInform ◽

10.1002/chin.199052183 ◽

1990 ◽

Vol 21 (52) ◽

Author(s):

L. F. TIETZE ◽

U. HARTFIEL

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Substituted 1

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

Canadian Journal of Chemistry ◽

10.1139/v06-124 ◽

2006 ◽

Vol 84 (10) ◽

pp. 1487-1503 ◽

Cited By ~ 19

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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