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Janus Face of the Steric Effect in a Lewis Acid Catalyst with Size-Exclusion Design: Steric Repulsion and Steric Attraction in the Catalytic Exo-Selective Diels–Alder Reaction

An exo-selective catalytic Diels–Alder reaction was developed using a Lewis acid catalyst with size-exclusion structural design. Exploiting the steric effect, especially the steric attraction, the Lewis acid catalyst was able… Click to show full abstract

An exo-selective catalytic Diels–Alder reaction was developed using a Lewis acid catalyst with size-exclusion structural design. Exploiting the steric effect, especially the steric attraction, the Lewis acid catalyst was able to reroute the reaction along a higher-energy pathway. The experimental findings were also supported by theoretical calculations. This catalyst development allows an easy and practical access to highly complex and pharmaceutically relevant compounds.

Keywords: lewis acid; diels alder; acid catalyst; reaction; exo selective

Journal Title: ACS Sustainable Chemistry & Engineering
Year Published: 2018

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