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

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 th...

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Published inJournal of organic chemistry Vol. 62; no. 10; pp. 3049 - 3054
Main Authors Sbai, Abdelouahid, Branchadell, Vicenç, Ortuño, Rosa Maria, Oliva, Antonio
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.05.1997
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Summary: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.
Bibliography:ark:/67375/TPS-DR3LHBNS-K
Abstract published in Advance ACS Abstracts, April 1, 1997.
istex:831B76CD65FDBA0F713CBC4922A1C9AC9BC64011
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo960447j