Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Guarnieri-Ibáñez, Alejandro
Medina, Florian
Besnard, Céline
Kidd, Sarah L
Spring, David R https://orcid.org/0000-0001-7355-2824
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.
Description
Keywords
3402 Inorganic Chemistry, 3405 Organic Chemistry, 34 Chemical Sciences
Journal Title
Chem Sci
Conference Name
Journal ISSN
2041-6520
2041-6539
2041-6539
Volume Title
8
Publisher
Royal Society of Chemistry (RSC)