2
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation

      research-article

      Read this article at

      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          The importance of axial chirality in enantioselective synthesis has been widely recognized for decades. The practical access to certain structures such as biaryl amino phenols known as NOBINs in enantiopure form, however, still remains a challenge. In drug delivery, the incorporation of axially chiral molecules in systematic screening has also received a great deal of interest in recent years, which calls for innovation and practical synthesis of structurally different axially chiral entities. Herein we present an operationally simple catalytic N-alkylation of sulfonamides using commercially available chiral amine catalysts to deliver two important classes of axially chiral compounds: structurally diverse NOBIN analogs as well as axially chiral N-aryl sulfonamides in excellent enantiopurity. Structurally related chiral sulfonamide has shown great potential in drug molecules but enantioselective synthesis of them has never been accomplished before. The practical catalytic procedures of our methods also bode well for their wide application in enantioselective synthesis.

          Abstract

          NOBINs and other axially chiral entities have received a great deal of interest in recent years. Here, the authors report the kinetic resolution of racemic amino phenols and the enantioselective preparation of axially chiral N-aryl sulfonamides with excellent level of enantiopurity and broad substrate scope.

          Related collections

          Most cited references33

          • Record: found
          • Abstract: not found
          • Article: not found

          Complete field guide to asymmetric BINOL-phosphate derived Brønsted acid and metal catalysis: history and classification by mode of activation; Brønsted acidity, hydrogen bonding, ion pairing, and metal phosphates.

            Bookmark
            • Record: found
            • Abstract: not found
            • Article: not found

            Atroposelective total synthesis of axially chiral biaryl natural products.

              Bookmark
              • Record: found
              • Abstract: not found
              • Article: not found

              Atroposelective Synthesis of Axially Chiral Biaryl Compounds

                Bookmark

                Author and article information

                Contributors
                kurti.laszlo@rice.edu
                zhaoyu@nus.edu.sg
                Journal
                Nat Commun
                Nat Commun
                Nature Communications
                Nature Publishing Group UK (London )
                2041-1723
                11 July 2019
                11 July 2019
                2019
                : 10
                : 3061
                Affiliations
                [1 ]ISNI 0000 0001 0307 1240, GRID grid.440588.5, Shaanxi Institute of Flexible Electronics, , Northwestern Polytechnical University, ; Xi’an, 710072 China
                [2 ]ISNI 0000 0001 2180 6431, GRID grid.4280.e, Department of Chemistry, , National University of Singapore, ; 3 Science Drive 3, Singapore, 117543 Singapore
                [3 ]ISNI 0000 0004 1936 8278, GRID grid.21940.3e, Department of Chemistry, , Rice University BioScience Research Collaborative, ; 6500 Main Street, Rm 380, Houston, TX 77030 USA
                Author information
                http://orcid.org/0000-0003-4357-455X
                http://orcid.org/0000-0002-9679-4057
                http://orcid.org/0000-0002-7520-8362
                http://orcid.org/0000-0001-8597-4717
                http://orcid.org/0000-0002-2944-1315
                Article
                10940
                10.1038/s41467-019-10940-4
                6624369
                31296858
                e43a30b4-5cd5-448d-9877-6c599ca50f2d
                © The Author(s) 2019

                Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

                History
                : 8 February 2019
                : 6 June 2019
                Funding
                Funded by: FundRef https://doi.org/10.13039/501100005049, A*STAR | Science and Engineering Research Council (Science and Engineering Research Council - A STAR);
                Award ID: R-143-000-648-305
                Award Recipient :
                Categories
                Article
                Custom metadata
                © The Author(s) 2019

                Uncategorized
                asymmetric catalysis,organocatalysis,synthetic chemistry methodology
                Uncategorized
                asymmetric catalysis, organocatalysis, synthetic chemistry methodology

                Comments

                Comment on this article