Accessing skeletal diversity using catalyst control: formation of n and n + 1 macrocyclic triazole rings.
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.
Kelly
Ann Rowley
AR
Chemical Biology Platform, Broad Institute of MIT and Harvard, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.
Wei
Jingqiang
J
Kesavan
Sarathy
S
Marié
Jean-Charles
JC
Windmon
Nicole
N
Young
Damian W
DW
Marcaurelle
Lisa A
LA
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D014230:Triazoles; D012428:Ruthenium