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Accessing Skeletal Diversity Using Catalyst Control: Formation of n and n + 1 Macrocyclic Triazole Rings

2009; American Chemical Society; Volume: 11; Issue: 11 Linguagem: Inglês

10.1021/ol900562u

1523-7060

Ann Rowley Kelly, Jingqiang Wei, Sarathy Kesavan, Jean‐Charles Marié, Nicole Windmon, Damian W. Young, Lisa A. Marcaurelle,

Cyclopropane Reaction Mechanisms

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.