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Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

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Abstract

Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of α-imino carbenes and oxetanes under Rh(II)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald–Hartwig and Pictet–Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained.

Graphical abstract: Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

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Publication details

The article was received on 01 Mar 2017, accepted on 05 Jun 2017 and first published on 12 Jun 2017


Article type: Edge Article
DOI: 10.1039/C7SC00964J
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

    A. Guarnieri-Ibáñez, F. Medina, C. Besnard, S. L. Kidd, D. R. Spring and J. Lacour, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC00964J

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