Organocatalytic Mannich Reactions on a Carbapenem Core - Synthesis of Mannich Bases and Bicyclic Diazanonanes

Organocatalytic Mannich Reactions on a Carbapenem Core - Synthesis of Mannich Bases and Bicyclic Diazanonanes

An efficient diastereoselective synthesis of carbapenem Mannich bases was developed using organocatalysis. This method also provides a route to new highly functionalized diazabicyclo[4.2.1]nonanes of proposed biological significance. A carbapenem intermediate undergoes organocatalytic Mannich reacti...

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Veröffentlicht in:European journal of organic chemistry 2014-04, Vol.2014 (11), p.2253-2260
Hauptverfasser: Cele, Zamani E. D., Pawar, Sachin A., Naicker, Tricia, Maguire, Glenn E. M., Arvidsson, Per I., Kruger, Hendrik G., Govender, Thavendran
Format: Artikel
Sprache:eng
Schlagworte:
Carbapenems
Lactams
Mannich bases
Medicin och hälsovetenskap
Nitrogen ­heterocycles
Organocatalysis
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Zusammenfassung:An efficient diastereoselective synthesis of carbapenem Mannich bases was developed using organocatalysis. This method also provides a route to new highly functionalized diazabicyclo[4.2.1]nonanes of proposed biological significance. A carbapenem intermediate undergoes organocatalytic Mannich reaction with anilines to give the corresponding Mannich bases. It reacts with aliphatic or benzylic amines to give highly functionalized diazabicyclo[4.2.1]nonanes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301823