Nickel-Catalyzed Enantioselective Cross-Coupling of N‑Hydroxyphthalimide Esters with Vinyl Bromides

Nickel-Catalyzed Enantioselective Cross-Coupling of N‑Hydroxyphthalimide Esters with Vinyl Bromides

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis­(N,N-dimethylamino)­ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 ex...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2017-04, Vol.19 (8), p.2150-2153
Hauptverfasser: Suzuki, Naoyuki, Hofstra, Julie L, Poremba, Kelsey E, Reisman, Sarah E
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
cross-coupling reactions
enantioselectivity
esters
Esters - chemistry
moieties
Nickel - chemistry
organobromine compounds
Oxidation-Reduction
Phthalimides - chemistry
reducing agents
Stereoisomerism
Temperature
Vinyl Compounds - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis­(N,N-dimethylamino)­ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b00793