Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Mechanisms and Origins of Selectivities of the Lewis Acid-Catalyzed Diels–Alder Reactions between Arylallenes and Acrylates

Mechanisms and Origins of Selectivities of the Lewis Acid-Catalyzed Diels–Alder Reactions between Arylallenes and Acrylates
Wei Li, K. N. Houk, Peiyuan Yu
The mechanisms of recently reported Lewis acid-catalyzed Diels–Alder reactions of arylallenes and acrylates were studied using density functional theory calculations. A stepwise mechanism involving short-lived zwitterion intermediates is established. The reaction is endo-selective in the presence of Lewis acid catalyst. The [2 + 2] cycloaddition is not observed because of the greater charge separation in the first step of the [2 + 2] cycloaddition. The origins of chirality transfer in the Diels–Alder reaction using chiral arylallenes are uncovered, and the absolute stereochemistry of the product is predicted.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01132

DOI: 10.1021/acs.joc.7b01132

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