Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N‑Heterobicyclic Enones

Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N‑Heterobicyclic Enones

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C–C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a...

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Veröffentlicht in:Journal of the American Chemical Society 2013-04, Vol.135 (13), p.4992-4995
Hauptverfasser: Shaw, Megan H, Melikhova, Ekaterina Y, Kloer, Daniel P, Whittingham, William G, Bower, John F
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Cyclopropanes - chemistry
Ketones - chemistry
Molecular Structure
Rhodium - chemistry
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Zusammenfassung:Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C–C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja401936c