Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts
JOURNAL OF ORGANIC CHEMISTRY, vol.78, no.4, pp.1604-1611, 2013 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 78 Issue: 4
- Publication Date: 2013
- Doi Number: 10.1021/jo302713b
- Journal Name: JOURNAL OF ORGANIC CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.1604-1611
- Open Archive Collection: AVESIS Open Access Collection
- Middle East Technical University Affiliated: Yes
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%).