Asymmetric Diels–Alder Reaction of Cyclopentadiene and Methyl Acrylate Catalyzed by Chiral Organoaluminum Reagents

1992 ◽  
Vol 65 (12) ◽  
pp. 3501-3503 ◽  
Author(s):  
Keiji Maruoka ◽  
Arnel B. Concepcion ◽  
Hisashi Yamamoto
Keyword(s):  
Methyl Acrylate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

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).

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.

The diels-alder reaction of cyclopentadiene and methyl acrylate on γ,-alumina

1990 ◽  
Vol 31 (38) ◽  
pp. 5433-5436 ◽  
Author(s):  
George Hondrogiannis ◽  
Richard M Pagni ◽  
George W Kabalka ◽  
Peter Anosike ◽  
Robert Kurt
Keyword(s):  
Methyl Acrylate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Diels-Alder Reaction of 1, 3-p-Menthadiene with Methyl Acrylate

1971 ◽  
Vol 92 (5) ◽  
pp. 437-440 ◽  
Author(s):  
Yoshiharu MATSUBARA ◽  
Wasaku MINEMATSU ◽  
Takao KISHIMOTO
Keyword(s):  
Methyl Acrylate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Diastereoselectivity and asymmetric induction in the Diels–Alder reaction of o-quinodimethanes

1986 ◽  
Vol 64 (4) ◽  
pp. 720-725 ◽  
Author(s):  
James L. Charlton
Keyword(s):  
Maleic Anhydride ◽  
Methyl Acrylate ◽  
Dimethyl Fumarate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Diels Alder Reaction ◽  
The Absolute ◽  
Alkoxy Groups

The extent of asymmetric induction in the bimolecular Diels–Alder reactions of chiral o-quinodimethanes with dimethyl fumarate, methyl acrylate, and maleic anhydride has been studied. o-Quinodimethanes with chiral α-alkoxy groups were prepared from 1-alkoxy-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4a–f or 1-alkoxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4g–h by thermolysis. These alkoxybenzosulfones were prepared from the corresponding hydroxybenzosulfones 8 and 1-phenylethanol, 2-phenyl-1-propanol, 4-phenyl-2-butanol, 1-phenyl-2-propanol, 3,3-dimethyl-2-butanol, or 1-cyclo-hexylethanol. The 1-phenylethoxy substituent yielded the largest asymmetric induction. The absolute configurations of the major cycloadducts of methyl acrylate with the o-quinodimethanes generated from 1-(R- 1-phenylethoxy)- and 1-(S-1-phenylethoxy)-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4i and 4j have been determined to be 1S,2S-1-(R-1-phenylethoxy)- and 1R,2R-1-(S-1-phenylethoxy)-2-carbomethoxy-1,2,3,4-tetrahydronaphthalene 11i and 11j, respectively. The proposition that a chiral alkoxy substituent can block one face of the o-quinodimethane towards addition of a dienophile is discussed.

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