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  Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters

Gatzenmeier, T., Turberg, M., Yepes, D., Xie, Y., Neese, F., Bistoni, G., et al. (2018). Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β - Unsaturated Methyl Esters. Journal of the American Chemical Society, 140(40), 12671-12676. doi:10.1021/jacs.8b07092.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0002-57A0-7 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-54BD-5
Genre: Journal Article

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Gatzenmeier, Turberg, Yepes, Xie, Neese, Bistoni, List 2018.pdf (Postprint), 2MB
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Gatzenmeier, Turberg, Yepes, Xie, Neese, Bistoni, List 2018.pdf
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 Creators:
Gatzenmeier, Tim1, Author           
Turberg, Mathias1, Author           
Yepes, Diana2, Author           
Xie, Youwei1, Author           
Neese, Frank3, Author           
Bistoni, Giovanni2, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541703              
3Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541710              

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 Abstract: Despite tremendous advances in enantioselective catalysis of the Diels−Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels−Alder methodology for a large
variety of α,β-unsaturated methyl esters and different dienes based on extremely reactive silylium imidodiphos-phorimidate (IDPi) Lewis acids. Mechanistic insights from accurate domain-based local pair natural orbital coupled-cluster (DLPNO-CCSD(T)) calculations rationalize the catalyst control and stereochemical outcome.

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Language(s): eng - English
 Dates: 2018-07-052018-10-022018-10-10
 Publication Status: Issued
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.8b07092
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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: 140 (40) Sequence Number: - Start / End Page: 12671 - 12676 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870