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Title: Activation of olefins via asymmetric Bronsted acid catalysis

Abstract

The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Bronsted 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 Bronsted 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 Bronsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. In conclusion, the methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.

Authors:
ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. Max-Planck-Institut fur Kohlenforschung, Mulheim an der Ruhr (Germany)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Max Planck Institute for Chemical Energy Conversion, Mulheim an der Ruhr (Germany)
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)
Sponsoring Org.:
USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR)
OSTI Identifier:
1454404
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Science
Additional Journal Information:
Journal Volume: 359; Journal Issue: 6383; Journal ID: ISSN 0036-8075
Publisher:
AAAS
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, and List, Benjamin. Activation of olefins via asymmetric Bronsted acid catalysis. United States: N. p., 2018. Web. doi:10.1126/science.aaq0445.
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Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, & List, Benjamin. Activation of olefins via asymmetric Bronsted acid catalysis. United States. https://doi.org/10.1126/science.aaq0445
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Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, and List, Benjamin. Fri . "Activation of olefins via asymmetric Bronsted acid catalysis". United States. https://doi.org/10.1126/science.aaq0445. https://www.osti.gov/servlets/purl/1454404.
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@article{osti_1454404,
title = {Activation of olefins via asymmetric Bronsted acid catalysis},
author = {Tsuji, Nobuya and Kennemur, Jennifer L. and Buyck, Thomas and Lee, Sunggi and Prevost, Sebastien and Kaib, Philip S. J. and Bykov, Dmytro and Fares, Christophe and List, Benjamin},
abstractNote = {The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Bronsted 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 Bronsted 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 Bronsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. In conclusion, the methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.},
doi = {10.1126/science.aaq0445},
journal = {Science},
number = 6383,
volume = 359,
place = {United States},
year = {Fri Mar 30 00:00:00 EDT 2018},
month = {Fri Mar 30 00:00:00 EDT 2018}
}
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https://doi.org/10.1126/science.aaq0445
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    Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination
    journal, January 2020

    • Yu, Zhang-Long; Cheng, Yong-Feng; Jiang, Na-Chuan
    • Chemical Science, Vol. 11, Issue 23
    • DOI: 10.1039/d0sc00001a

    Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates
    journal, October 2018

    • Schreyer, Lucas; Kaib, Philip S. J.; Wakchaure, Vijay N.
    • Science, Vol. 362, Issue 6411
    • DOI: 10.1126/science.aau0817

    Multilayer 3D Chirality and Its Synthetic Assembly
    journal, June 2019

    Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation
    journal, August 2018

    • Xu, Chao; Muir, Calum W.; Leach, Andrew G.
    • Angewandte Chemie, Vol. 130, Issue 35
    • DOI: 10.1002/ange.201806956

    Chiral Brønsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes
    journal, April 2019

    • Lin, Jin‐Shun; Li, Tao‐Tao; Jiao, Guan‐Yuan
    • Angewandte Chemie, Vol. 131, Issue 21
    • DOI: 10.1002/ange.201900955

    A multi-substrate screening approach for the identification of a broadly applicable Diels–Alder catalyst
    journal, February 2019

    Multilayer 3D Chirality and Its Synthetic Assembly
    journal, June 2019

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