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Synfacts 2019; 15(06): 0617
DOI: 10.1055/s-0037-1612553
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Alkyne–Azide Cycloaddition by Kinetic Resolution

Contributor(s):
Paul Knochel
,
Juri Skotnitzki
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
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Further Information

Publication History

Publication Date:
20 May 2019 (online)

 
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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.


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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.


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