8
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: not found
      • Article: not found

      Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis

      ,
      Angewandte Chemie International Edition
      Wiley-Blackwell

      Read this article at

      ScienceOpenPublisher
      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

          Related collections

          Most cited references45

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

          A powerful chiral counterion strategy for asymmetric transition metal catalysis.

          Traditionally, transition metal-catalyzed enantioselective transformations rely on chiral ligands tightly bound to the metal to induce asymmetric product distributions. Here we report high enantioselectivities conferred by a chiral counterion in a metal-catalyzed reaction. Two different transformations catalyzed by cationic gold(I) complexes generated products in 90 to 99% enantiomeric excess with the use of chiral binaphthol-derived phosphate anions. Furthermore, we show that the chiral counterion can be combined additively with chiral ligands to enable an asymmetric transformation that cannot be achieved by either method alone. This concept of relaying chiral information via an ion pair should be applicable to a vast number of metal-mediated processes.
            Bookmark
            • Record: found
            • Abstract: not found
            • Article: not found

            Asymmetric Ion-Pairing Catalysis

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

              The progression of chiral anions from concepts to applications in asymmetric catalysis.

              Despite the tremendous advances of the past four decades, chemists are far from being able to use chiral catalysts to control the stereoselectivity of any desired reaction. New concepts for the construction and mode of operation of chiral catalysts have the potential to open up previously inaccessible reaction space. The recognition and categorization of distinct approaches seems to play a role in triggering rapid exploration of new territory. This Review both reflects on the origins as well as details a selection of the latest examples of an area that has advanced considerably within the past five years or so: the use of chiral anions in asymmetric catalysis. Defining reactions as involving chiral anions is a difficult task owing to uncertainties over the exact catalytic mechanisms. Nevertheless, we attempt to provide an overview of the breadth of reactions that could reasonably fall under this umbrella.
                Bookmark

                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley-Blackwell
                14337851
                December 19 2016
                December 19 2016
                : 55
                : 51
                : 15889-15893
                Article
                10.1002/anie.201609095
                aa90cf9b-8f8d-4810-969d-16c80c87479d
                © 2016

                http://doi.wiley.com/10.1002/tdm_license_1.1

                History

                Comments

                Comment on this article