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  Unveiling the Delicate Balance of Steric and Dispersion Interactions in Organocatalysis Using High-Level Computational Methods

Yepes, D., Neese, F., List, B., & Bistoni, G. (2020). Unveiling the Delicate Balance of Steric and Dispersion Interactions in Organocatalysis Using High-Level Computational Methods. Journal of the American Chemical Society, 142(7), 3613-3625. doi:10.1021/jacs.9b13725.

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 Creators:
Yepes, Diana1, Author           
Neese, Frank2, Author           
List, Benjamin3, Author           
Bistoni, Giovanni1, Author           
Affiliations:
1Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541703              
2Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541710              
3Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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 Abstract: High-level quantum electronic structure calculations are used to provide a deep insight into the mechanism and stereocontrolling factors of two recently developed catalytic asymmetric Diels–Alder (DA) reactions of cinnamate esters with cyclopentadiene. The reactions employ two structurally and electronically very different in situ silylated enantiopure Lewis acid organocatalysts: i.e., binaphthyl-allyl-tetrasulfone (BALT) and imidodiphosphorimidate (IDPi). Each of these catalysts activates only specific substrates in an enantioselective fashion. Emphasis is placed on identifying and quantifying the key noncovalent interactions responsible for the selectivity of these transformations, with the final aim of aiding in the development of designing principles for catalysts with a broader scope. Our results shed light into the mechanism through which the catalyst architecture determines the selectivity of these transformations via a delicate balance of dispersion and steric interactions.

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Language(s): eng - English
 Dates: 2019-12-202020-01-272020-02-19
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.9b13725
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 142 (7) Sequence Number: - Start / End Page: 3613 - 3625 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870