Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts


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Isik M., TANYELİ C.

JOURNAL OF ORGANIC CHEMISTRY, vol.78, no.4, pp.1604-1611, 2013 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 78 Issue: 4
  • Publication Date: 2013
  • Doi Number: 10.1021/jo302713b
  • Title of Journal : JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.1604-1611

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-beta-nitroolefins with good to excellent yields (87-93%) and enantioselectivites (up to 99%).