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

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2013-02-15
Isik, Murat
Tanyeli, Cihangir
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%).