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.
Recommended Citation
E. C. Liu and J. J. Topczewski, "Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution," Journal of the American Chemical Society, vol. 141, no. 13, pp. 5135 - 5138, American Chemical Society, Apr 2019.
The definitive version is available at https://doi.org/10.1021/jacs.9b01091
Department(s)
Chemistry
International Standard Serial Number (ISSN)
1520-5126; 0002-7863
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2025 American Chemical Society, All rights reserved.
Publication Date
03 Apr 2019
PubMed ID
30888164
Comments
National Institutes of Health, Grant R35GM124718