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Skeletal Editing—Nitrogen Deletion of Secondary Amines by Anomeric Amide Reagents

Zippel, Christoph 1; Seibert, Jasmin 1; Bräse, Stefan 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


Late-stage modification is highly desirable for the diversification and modification of biologically active compounds. Peripheral editing (e.g., C−H activation) has been the predominant methodology, whereas skeletal editing is in its infancy. The single-atom N-deletion using anomeric amide reagents constitutes a powerful tool to modify the underlying molecular skeletons of secondary amines. N-pivaloyloxy-N-alkoxyamide is easily prepared on a large scale and promotes C−C bond formation in good yields under the extrusion of N2 for a variety of (cyclic) aliphatic amines. The exploitation of widely available amines allows the use of existing amine synthesis protocols to translate into the construction of new C−C bonds, enabling ring contraction and the potential for structure optimization of biologically active compounds.

Verlagsausgabe §
DOI: 10.5445/IR/1000136392
Veröffentlicht am 16.08.2021
DOI: 10.1002/anie.202107490
Zitationen: 21
Web of Science
Zitationen: 20
Zitationen: 24
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 1433-7851, 1521-3773
KITopen-ID: 1000136392
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Angewandte Chemie / International edition
Verlag John Wiley and Sons
Band 60
Heft 36
Seiten 19522-19524
Vorab online veröffentlicht am 01.08.2021
Nachgewiesen in Dimensions
Web of Science
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