A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides

Author:

Jacob Clément,Baguia Hajar,Dubart Amaury,Oger Samuel,Thilmany Pierre,Beaudelot Jérôme,Deldaele Christopher,Peruško Stefano,Landrain Yohann,Michelet BastienORCID,Neale SamuelORCID,Romero Eugénie,Moucheron CécileORCID,Van Speybroeck VeroniqueORCID,Theunissen CédricORCID,Evano GwilhermORCID

Abstract

AbstractA general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway.

Funder

Belgian National Fund for Scientific Research | Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture

Fonds Wetenschappelijk Onderzoek

Research Board of the Ghent University

Innoviris

Ghent University (Stevin Supercomputer Infrastructure) VSC

Fonds De La Recherche Scientifique - FNRS

Publisher

Springer Science and Business Media LLC

Subject

General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary

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