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Title

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

Authors
Kidd, Sarah L.
Spring, David R.
Published in Chemical Science. 2017, vol. 8, no. 8, p. 5713-5720
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.
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Research group Groupe Lacour
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GUARNIERI IBANEZ, Alejandro José et al. Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes. In: Chemical Science, 2017, vol. 8, n° 8, p. 5713-5720. https://archive-ouverte.unige.ch/unige:95630

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Deposited on : 2017-07-25

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