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

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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 4; pp. 1604 - 1611
Main Authors Isik, Murat, Tanyeli, Cihangir
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.02.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-AMINOPYRIDINIUM IONS
THIOACETIC ACID
KINETIC RESOLUTION
1,3-DICARBONYL COMPOUNDS
ARYL HALIDES
ASYMMETRIC MICHAEL ADDITION
BASE CATALYSTS
CHIRAL PROTON CATALYSIS
ENANTIOSELECTIVE ACYL TRANSFER
CONJUGATE ADDITION
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Summary: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%).
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo302713b