Roles of Lewis Acid Catalysts in Diels-Alder Reactions between Cyclopentadiene and Methyl Acrylate.

ChemistryOpen
Ken Sakata, Hiroshi Fujimoto

Abstract

The Diels-Alder reaction of cyclopentadiene with methyl acrylate catalyzed by AlCl3 has been theoretically investigated. M06-2X level DFT calculations have shown that the formation of two C-C bonds is asynchronous in the cycloaddition both in the endo path and in the exo path, thus making a good contrast to the well-known concept of [4+2] reactions based on the orbital symmetry arguments. It was found that the catalyst facilitates the cycloaddition and brings a higher endo selectivity in the highly asynchronous process, as compared with the reaction of the diene and the dienophile without the catalyst.

References

May 18, 2000·The Journal of Organic Chemistry·S Yamabe, T Minato
Oct 25, 2001·The Journal of Organic Chemistry·Masahiro ImadeHiroshi Fujimoto
Jul 23, 2004·The Journal of Chemical Physics·Hrant P Hratchian, H Bernhard Schlegel
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Jan 12, 2008·Accounts of Chemical Research·Yan Zhao, Donald G Truhlar
Aug 21, 2008·Journal of the American Chemical Society·Ken Sakata, Hiroshi Fujimoto
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Jul 10, 2009·The Journal of Chemical Physics·Peifeng Su, Hui Li
May 17, 2002·Angewandte Chemie·K C NicolaouGeorgios Vassilikogiannakis
Feb 5, 2013·The Journal of Organic Chemistry·Ken Sakata, Hiroshi Fujimoto

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Citations

Jun 8, 2021·Chemical Science·Pascal VermeerenF Matthias Bickelhaupt

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