Abstract
An enantioselective copper-catalyzed azide-alkyne cycloaddition (E-CuAAC) is reported by kinetic resolution. Chiral triazoles were isolated in high yield with limiting alkyne (up to 97:3 enantiomeric ratio (er)). A range of substrates were tolerated (>30 examples), and the reaction was scaled to >1 g. The er of a triazole product could be enhanced by recrystallization and the recovered scalemic azide could be racemized and recycled. Recycling the azide allows efficient use of the undesired azide enantiomer.
Recommended Citation
J. R. Alexander et al., "Kinetic Resolution Of Cyclic Secondary Azides, Using An Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition," Organic Letters, vol. 21, no. 11, pp. 4355 - 4358, American Chemical Society, Jun 2019.
The definitive version is available at https://doi.org/10.1021/acs.orglett.9b01556
Department(s)
Chemistry
International Standard Serial Number (ISSN)
1523-7052; 1523-7060
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2025 American Chemical Society, All rights reserved.
Publication Date
07 Jun 2019
PubMed ID
31117717
Comments
National Institutes of Health, Grant S10OD011952