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
Reference53 articles.
1. Bon, R. S. & Waldmann, H. Bioactivity-guided navigation of chemical space. Acc. Chem. Res. 43, 1103–1114 (2010).
2. Qureshi, M. H. Top 200 Pharmaceuticals by Retail Sales in 2020. https://njardarson.lab.arizona.edu/sites/njardarson.lab.arizona.edu/files/Top%20200%20Pharmaceuticals%20By%20Retail%20Sales%202020V3.pdf (2020).
3. Baldwin, J. E. Rules for ring closure. J. Chem. Soc., Chem. Commun. 734–736 (1976).
4. Gilmore, K. & Alabugin, I. V. Cyclizations of alkynes: revisiting Baldwin’s Rules for ring closure. Chem. Rev. 111, 6513–6556 (2011).
5. Gilmore, K., Mohamed, R. K. & Alabugin, I. V. The Baldwin Rules: revised and extended. WIREs Comput. Mol. Sci. 6, 487–514 (2016).
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