Abstract
The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
Recommended Citation
E. C. Liu and J. J. Topczewski, "Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution," Journal of the American Chemical Society, vol. 143, no. 14, pp. 5308 - 5313, American Chemical Society, Apr 2021.
The definitive version is available at https://doi.org/10.1021/jacs.1c01354
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
14 Apr 2021
PubMed ID
33798335
Comments
National Institutes of Health, Grant S10OD011952