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 in | Journal of organic chemistry Vol. 62; no. 10; pp. 3049 - 3054 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
16.05.1997
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Online Access | Get full text |
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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. |
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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 |