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

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.

SUBMITTER: Sakata K 

PROVIDER: S-EPMC7269005 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature