Cu-Catalyzed Selective Mono-N-pyridylation: Direct Access to 2-AminoDMAP/Sulfonamides as Bifunctional Organocatalysts
JOURNAL OF ORGANIC CHEMISTRY, cilt.78, sa.4, ss.1604-1611, 2013 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 78 Sayı: 4
- Basım Tarihi: 2013
- Doi Numarası: 10.1021/jo302713b
- Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1604-1611
- Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
- Orta Doğu Teknik Üniversitesi Adresli: Evet
Özet
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%).