Origin of rate enhancement and asynchronicity in iminium catalyzed Diels–Alder reactions-Reference-Cited by-同舟云学术

Origin of rate enhancement and asynchronicity in iminium catalyzed Diels–Alder reactions

Published:2020 Issue:31 Volume:11 Page:8105-8112
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Vermeeren Pascal¹²³⁴⁵^ORCID,Hamlin Trevor A.¹²³⁴⁵^ORCID,Fernández Israel⁶⁷⁸⁹¹⁰^ORCID,Bickelhaupt F. Matthias¹²³⁴⁵^ORCID

Affiliation:

1. Department of Theoretical Chemistry

2. Amsterdam Institute of Molecular and Life Sciences (AIMMS)

3. Amsterdam Center for Multiscale Modeling (ACMM)

4. Vrije Universiteit Amsterdam

5. 1081 HV Amsterdam

6. Departamento de Química Orgánica I

7. Centro de Innovación en Química Avanzada (ORFEO-CINQA)

8. Facultad de Ciencias Químicas

9. Universidad Complutense de Madrid

10. 28040 Madrid

Abstract

Quantum chemical activation strain analyses revealed that iminium catalysts accelerate Diels–Alder reactions by reducing the Pauli repulsion between reactants.

Funder

Ministerio de Economía y Competitividad

Nederlandse Organisatie voor Wetenschappelijk Onderzoek

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/SC/D0SC02901G

Reference47 articles.

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2. Iminium Catalysis

3. The Fluorine-Iminium IonGaucheEffect: Proof of Principle and Application to Asymmetric Organocatalysis

4. Cyclopropyl Iminium Activation: Reactivity Umpolung in Enantioselective Organocatalytic Reaction Design

5. Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation

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