Kinetic diastereomer differentiation in Au(III)- and Bi(III)-catalyzed benzylic arylation: concise and stereocontrolled synthesis of 2-amino-1,1-diarylalkanes.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
Read More Add to Saved list
  • Author(s): Chénard E;Chénard E; Hanessian S
  • Source:
    Organic letters [Org Lett] 2014 May 16; Vol. 16 (10), pp. 2668-71. Date of Electronic Publication: 2014 May 07.
  • Publication Type:
    Journal Article; Research Support, Non-U.S. Gov't
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE
    • Publication Information:
      Original Publication: Washington, DC : American Chemical Society, c1999-
    • Subject Terms:
      Alkanes/*chemical synthesis ; Benzyl Alcohols/*chemistry ; Bismuth/*chemistry ; Gold/*chemistry; Alkanes/chemistry ; Azides/chemical synthesis ; Azides/chemistry ; Catalysis ; Kinetics ; Lewis Acids/chemistry ; Molecular Structure ; Nitro Compounds/chemical synthesis ; Nitro Compounds/chemistry ; Stereoisomerism
    • Abstract:
      Benzylic alcohols carrying an adjacent α-nitro or α-azido group on the alkane chain are converted into syn-1,1-diaryl-2-nitro- and 2-azidoalkanes with electron-rich arenes in stereoselective reactions catalyzed by Brønsted and Lewis acids. Gold(III) chloride and bismuth(III) triflate were found to be especially efficient as catalysts, showing kinetically controlled differentiation in the reactivity of diastereomeric α-substituted benzyl alcohols. Applications to therapeutically relevant syn- and anti- 2-amino-1,1-diarylalkanes are projected.
    • Accession Number:
      0 (Alkanes)
      0 (Azides)
      0 (Benzyl Alcohols)
      0 (Lewis Acids)
      0 (Nitro Compounds)
      7440-57-5 (Gold)
      U015TT5I8H (Bismuth)
    • Publication Date:
      Date Created: 20140509 Date Completed: 20140721 Latest Revision: 20140516
    • Publication Date:
      20240829
    • Accession Number:
      10.1021/ol500902p
    • Accession Number:
      24805004