Liu E.-C,
Topczewski JJ.
* University of Minnesota, minneapolis, USA
Enantioselective Copper Catalyzed Alkyne–Azide Cycloaddition by Dynamic Kinetic Resolution.
J. Am. Chem. Soc. 2019;
141: 5135-5138
Key words
copper catalysis - alkynes - azides - cycloaddition - kinetic resolution
Significance
Liu and Topczewski report a copper-catalyzed alkyne–azide cycloaddition by dynamic
kinetic resolution (DKR) leading to α-chiral triazoles in high yields. Due to the
broad scope and the extension to complex fragments, this method should be of great
interest for organic synthesis.
Comment
Interestingly, the diastereoselectivity was reversed by changing the stereochemistry
of the ligand, showing the utility of this method. As an extension, derivatives of
vitamin E, gibberellic acid, esterone, glucose, mycophenolate mofetil and moexipril
were successfully functionalized.
