Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes.

Autor:	Boyd O; School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK., Wang GW; School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK., Sokolova OO; School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK., Calow ADJ; School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK., Bertrand SM; GlaxoSmithKline R&D, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK., Bower JF; School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.
Jazyk:	angličtina
Zdroj:	Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Dec 19; Vol. 58 (52), pp. 18844-18848. Date of Electronic Publication: 2019 Nov 21.
DOI:	10.1002/anie.201910276
Abstrakt:	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. (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze:	MEDLINE
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