Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study

Abdelouahid Sbai; Vicenç Branchadell; Rosa Maria Ortuño; Antonio Oliva

doi:10.1021/jo960447j

Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study

Abdelouahid Sbai, Vicenç Branchadell, Rosa Maria Ortuño, Antonio Oliva

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

48 Citations (Scopus)

Abstract

The Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl3 have been theoretically studied at the B-LYP/6-31G* level. The results obtained show that the catalyst increases both the endo / exo and syn / anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.

Original language	English
Pages (from-to)	3049-3054
Journal	Journal of Organic Chemistry
Volume	62
Issue number	10
DOIs	https://doi.org/10.1021/jo960447j
Publication status	Published - 1 Dec 1997

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title = "Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study",

abstract = "The Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl3 have been theoretically studied at the B-LYP/6-31G* level. The results obtained show that the catalyst increases both the endo / exo and syn / anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.",

author = "Abdelouahid Sbai and Vicen{\c c} Branchadell and Ortu{\~n}o, {Rosa Maria} and Antonio Oliva",

year = "1997",

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doi = "10.1021/jo960447j",

language = "English",

volume = "62",

pages = "3049--3054",

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Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study. / Sbai, Abdelouahid; Branchadell, Vicenç ; Ortuño, Rosa Maria ; Oliva, Antonio.

In: Journal of Organic Chemistry, Vol. 62, No. 10, 01.12.1997, p. 3049-3054.

Research output: Contribution to journal › Article › Research › peer-review

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T1 - Effect of Lewis Acid Catalysis on the Diels-Alder Reaction between Methyl (Z)-(S)-4,5-(2,2-Propylidenedioxy)pent-2-enoate and Cyclopentadiene. A Theoretical Study

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AU - Branchadell, Vicenç

AU - Ortuño, Rosa Maria

AU - Oliva, Antonio

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N2 - The Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl3 have been theoretically studied at the B-LYP/6-31G* level. The results obtained show that the catalyst increases both the endo / exo and syn / anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.

AB - The Diels-Alder reactions of methyl (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoate and (Z)-(S)-4,5-(2,2-propylidenedioxy)pent-2-enoic acid with cyclopentadiene catalyzed by AlCl3 have been theoretically studied at the B-LYP/6-31G* level. The results obtained show that the catalyst increases both the endo / exo and syn / anti selectivity, in good qualitative agreement with the experimental observations. The origin of the selectivity and the role of the catalyst are discussed.

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