Front cover artwork - Bifunctional Hydrogen Bond Donor‐Catalyzed Diels–Alder Reactions: Origin of Stereoselectivity and Rate Enhancement

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Abstract

(Thio)ureas have found numerous applications as organocatalysts, yet their mode of action, that is, the mechanism by which they accelerate reactions is still not fully understood. In this work, quantum chemical activation strain analyses reveal that these bifunctional hydrogen bond organocatalysts accelerate the Diels–Alder reaction between cyclopentadiene and acrolein by reducing the two-center four-electron (steric) Pauli repulsion between the occupied π-orbitals of the reactants and not by enhancing the donor–acceptor orbital interactions, as is traditionally considered. More information can be found in the Full Paper by P. Vermeeren, T. A. Hamlin, F. M. Bickelhaupt, and I. Fernández on page 5180. Read the full text of this paper at 10.1002/chem.202005344
Original languageEnglish
Edition16
DOIs
Publication statusPublished - 17 Mar 2021

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