Intramolecular Amido Transfer Leading to Structurally Diverse Nitrogen-Containing Macrocycles

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Reported herein is the development of rhodium-catalyzed intramolecular amido transfer as an efficient route to nitrogen-containing macrocycles starting from acetophenone ketoximes tethered with either aryl or alkyl azides. Facile generation of rhodacycles and metal imido intermediates was the key to success in this mechanistic scaffold to represent the first example of an intramolecular inner-sphere C-H amination. While substrates bearing aryl azides underwent a monomeric ring formation in high yields, a dimeric double cyclization took place exclusively with alkyl-azide-tethered ketoximes, thus affording up to 36-membered azamacrocyclic products.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2017-03
Language
English
Article Type
Article
Keywords

C-H AMINATION; N BOND FORMATION; INTERMOLECULAR AMINATION; ALKYL AZIDES; FUNCTIONALIZATION; AMIDATION; ACTIVATION; C(SP(3))-H; CARBAZOLES; METATHESIS

Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.56, no.12, pp.3344 - 3348

ISSN
1433-7851
DOI
10.1002/anie.201700113
URI
http://hdl.handle.net/10203/223236
Appears in Collection
CH-Journal Papers(저널논문)
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