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. 2009 Jun 4;11(11):2257-60.
doi: 10.1021/ol900562u.

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

Ann Rowley Kelly  1 , Jingqiang Wei, Sarathy Kesavan, Jean-Charles Marié, Nicole Windmon, Damian W Young, Lisa A Marcaurelle
Affiliations

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

Ann Rowley Kelly et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Use of Huisgen cycloaddition for divergent pairing
Scheme 2
Scheme 2
Substrate synthesis and intramolecular Ru-catalyzed cycloaddition
Figure 1
Figure 1
X-ray crystal structures of representative macrocyclic triazoles (4a and 5f)
See this image and copyright information in PMC

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