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

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2013-02-15

Author

Isik, Murat
Tanyeli, Cihangir

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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%).

Subject Keywords

Organocatalysts, Copper, Aromatic compounds, Selectivity, Catalysts

URI

https://hdl.handle.net/11511/38052

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo302713b

Collections

Department of Chemistry, Article

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Citation Formats

M. Isik and C. Tanyeli, “Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts,” JOURNAL OF ORGANIC CHEMISTRY, pp. 1604–1611, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38052.