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- Title
Modular Access to Eight‐Membered N‐Heterocycles by Directed Carbonylative C−C Bond Activation of Aminocyclopropanes.
- Authors
Boyd, Olivia; Wang, Gang‐Wei; Sokolova, Olga O.; Calow, Adam D. J.; Bertrand, Sophie M.; Bower, John F.
- Abstract
Aminocyclopropanes equipped with pendant nucleophiles undergo carbonylative heterocyclization triggered by C−C bond activation to generate eight‐membered N‐heterocycles. In these processes, intramolecular "capture" of a rhodacyclopentanone intermediate by an aryl or N‐based nucleophile is followed by C−C or C−N bond‐forming "collapse" to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.
- Subjects
METALLACYCLES; NUCLEOPHILES; CYCLOPROPANE; RHODIUM
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 52, p19020
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201910276