Author:
Brittain William D. G.,Dalling Andrew G.,Sun Zhenquan,Duff Cécile S. Le,Male Louise,Buckley Benjamin R.,Fossey John S.
Abstract
Abstract
A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.
Funder
Wellcome Trust
The Royal Society of Chemistry
The Society for Chemical Industry
The Royal Society
Research Councils UK
EPSRC
Publisher
Springer Science and Business Media LLC
Reference47 articles.
1. Lewis, W. G. et al. Click Chemistry In Situ: Acetylcholinesterase as a Reaction Vessel for the Selective Assembly of a Femtomolar Inhibitor from an Array of Building Blocks. Angew. Chem. Int. Ed. 41, 1053-1057, 10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4 (2002).
2. Tornøe, C. W., Christensen, C. & Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. J. Org. Chem. 67, 3057–3064,
https://doi.org/10.1021/jo011148j
(2002).
3. Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. Engl. 40, 2004–2021 (2001).
4. Meldal, M. & Tornøe, C. W. Cu-Catalyzed Azide−Alkyne Cycloaddition. Chem. Rev. 108, 2952–3015,
https://doi.org/10.1021/cr0783479
(2008).
5. Thirumurugan, P., Matosiuk, D. & Jozwiak, K. Click Chemistry for Drug Development and Diverse Chemical–Biology Applications. Chem. Rev. 113, 4905–4979,
https://doi.org/10.1021/cr200409f
(2013).
Cited by
13 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献