List   Previous   Next  

Publication 184  

  1. Diversity-Oriented Synthesis of Heterocycles and Macrocycles by Controlled Reactions of Oxetanes and α-Iminocarbenes
    Alejandro Guarnieri-Ibáñez, Florian Medina, Céline Besnard, Sarah L. Kidd, David R. Spring, Jérôme Lacour
    Chem. Sci. 2017, 8, 5713-5720

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 clues were obtained

DOI: 10.1039/C7SC00964J 

open archive unige:95630