Cu-catalyzed selective mono-N-pyridylation: Direct access to 2-aminoDMAP/sulfonamides as bifunctional organocatalysts
Author
Isik, M.
Tanyeli, C.
Date
2013Source Title
Journal of Organic Chemistry
Print ISSN
223263
Volume
78
Issue
4
Pages
1604 - 1611
Language
English
Type
ArticleItem 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
AcetylacetoneAsymmetric conjugate addition
Bi-functional
Cu catalysis
Enantioselectivites
Facile preparation
Nitroolefins
Organocatalysts
Acetone
Catalysis
Catalysts
acetylacetone
copper
sulfonamide
article
catalysis
catalyst
chemical reaction
chirality
enantioselectivity