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Org Lett DOI:10.1021/ol900562u

Accessing skeletal diversity using catalyst control: formation of n and n + 1 macrocyclic triazole rings.

Publication TypeJournal Article
Year of Publication2009
AuthorsKelly, ARowley, Wei, J, Kesavan, S, Marie, J-C, Windmon, N, Young, DW, Marcaurelle, LA
JournalOrg Lett
Volume11
Issue11
Pages2257-60
Date Published2009 Jun 04
ISSN1523-7052
KeywordsAlkynes, Catalysis, Combinatorial Chemistry Techniques, Cyclization, Molecular Structure, Ruthenium, Triazoles
Abstract

A regioselective intramolecular Huisgen cycloaddition was performed on various azido alkyne substrates giving rise to macrocyclic triazole rings. Using catalyst control, a common intermediate has been converted to two structurally unique macrocycles with either a 1,5- or a 1,4-triazole resulting in an n or n + 1 ring size. This is the first example of an intramolecular ruthenium-catalyzed Huisgen cycloaddition.

URLhttp://dx.doi.org/10.1021/ol900562u
DOI10.1021/ol900562u
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/19473044?dopt=Abstract

Alternate JournalOrg. Lett.
PubMed ID19473044
PubMed Central IDPMC2702139
Grant ListP50 GM069721 / GM / NIGMS NIH HHS / United States
P50 GM069721-07 / GM / NIGMS NIH HHS / United States