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      Cu-catalyzed selective mono-N-pyridylation: Direct access to 2-aminoDMAP/sulfonamides as bifunctional organocatalysts

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      Author
      Isik, M.
      Tanyeli, C.
      Date
      2013
      Source Title
      Journal of Organic Chemistry
      Print ISSN
      223263
      Volume
      78
      Issue
      4
      Pages
      1604 - 1611
      Language
      English
      Type
      Article
      Item Usage Stats
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      Abstract
      Direct and selective mono-N-pyridylation of trans-(R,R)-cyclohexane-1,2- diamine is described here. Facile preparation of a novel chiral 2-aminoDMAP core catalaphore via Cu catalysis has led to the development of various sulfonamide/2-aminoDMAPs as bifunctional acid/base organocatalysts (most in two steps overall), which have been shown to very effectively promote asymmetric conjugate addition of acetylacetone to trans-β-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%). © 2013 American Chemical Society.
      Keywords
      Acetylacetone
      Asymmetric conjugate addition
      Bi-functional
      Cu catalysis
      Enantioselectivites
      Facile preparation
      Nitroolefins
      Organocatalysts
      Acetone
      Catalysis
      Catalysts
      acetylacetone
      copper
      sulfonamide
      article
      catalysis
      catalyst
      chemical reaction
      chirality
      enantioselectivity
      Permalink
      http://hdl.handle.net/11693/21071
      Published Version (Please cite this version)
      http://dx.doi.org/10.1021/jo302713b
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      • Institute of Materials Science and Nanotechnology (UNAM) 1775
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