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

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.

SUBMITTER: Kelly AR

PROVIDER: S-EPMC2702139 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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

Kelly Ann Rowley AR Wei Jingqiang J Kesavan Sarathy S Marié Jean-Charles JC Windmon Nicole N Young Damian W DW Marcaurelle Lisa A LA

Organic letters 20090601 11

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. ...[more]

PMID: 19473044

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