Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

En Chih Liu, Joseph J Topczewski

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would enable the direct synthesis of α-chiral triazoles. Doing so is demanding because the two precursors have linear geometries, and the triazole product is a flat heterocycle. Designing a chiral catalyst is further complicated by the complex mechanism of CuAAC. We report an enantioselective CuAAC (E-CuAAC), enabled by dynamic kinetic resolution (DKR). The E-CuAAC is high yielding and affords up to 99:1 er. The E-CuAAC can directly generate α-chiral triazoles in a complex molecular environment.

Original languageEnglish (US)
Pages (from-to)5135-5138
Number of pages4
JournalJournal of the American Chemical Society
Volume141
Issue number13
DOIs
StatePublished - Apr 3 2019

Bibliographical note

Funding Information:
We acknowledge the University of Minnesota and The American Chemical Society’s Petroleum Research Fund (PRF #56505-DNI1) for financial support. This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718.

Funding Information:
We acknowledge the University of Minnesota and The American Chemical Society???s Petroleum Research Fund (PRF #56505- DNI1) for financial support. This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718.

Publisher Copyright:
© 2019 American Chemical Society.

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