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  Activation of olefins via asymmetric Brønsted acid catalysis

Tsuji, N., Kennemur, J. L., Buyck, T., Lee, S., Prévost, S., Kaib, P. S. J., et al. (2018). Activation of olefins via asymmetric Brønsted acid catalysis. Science, 359(6383), 1501-1505. doi:10.1126/science.aaq0445.

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Tsuji, Kennemur, Buyck, Lee, Prevost, Kaib, Bykov, Fares, List 2018.pdf (Postprint), 689KB
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Tsuji, Kennemur, Buyck, Lee, Prevost, Kaib, Bykov, Fares, List 2018.pdf
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 Creators:
Tsuji, Nobuya1, Author              
Kennemur, Jennifer L.1, Author              
Buyck, Thomas1, Author              
Lee, Sunggi1, Author              
Prévost, Sébastien1, Author              
Kaib, Philip S. J.1, Author              
Bykov, Dmytro2, 3, Author
Farès, Christophe4, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2National Center for Computational Sciences, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA, ou_persistent22              
3Max Planck Institute for Chemical Energy Conversion, Stiftstraße 34–36, 45470 Mülheim an der Ruhr, Germany., ou_persistent22              
4Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 Abstract: The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Brønsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Brønsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Brønsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. The methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.

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Language(s): eng - English
 Dates: 2017-09-252018-02-022018-03-30
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1126/science.aaq0445
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Title: Science
  Abbreviation : Science
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Association for the Advancement of Science
Pages: - Volume / Issue: 359 (6383) Sequence Number: - Start / End Page: 1501 - 1505 Identifier: ISSN: 0036-8075
CoNE: https://pure.mpg.de/cone/journals/resource/991042748276600_1