The donation of phytosphingosine by T. Böhmer, Evonik-Industries, Essen (Germany) is highly appreciated. This work was in part financed by a WGL-PFI project.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/olbannercenter.gif?v=1&s=c083e1920cd41ed129901c116018eab93b5ad3c4)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide–Alkyne Cycloaddition†
Article first published online: 18 APR 2012
DOI: 10.1002/anie.201108850
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
van Berkel, S. S., Brauch, S., Gabriel, L., Henze, M., Stark, S., Vasilev, D., Wessjohann, L. A., Abbas, M. and Westermann, B. (2012), Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide–Alkyne Cycloaddition . Angew. Chem. Int. Ed., 51: 5343–5346. doi: 10.1002/anie.201108850
- †
Publication History
- Issue published online: 23 MAY 2012
- Article first published online: 18 APR 2012
Funded by
- WGL-PFI project
Keywords:
- bioconjugation;
- click chemistry;
- nitrogen heterocycles;
- Sakai reaction
Triple-T trick! Traceless tosylhydrazone-based triazole formation is readily achieved by reacting primary amines with functional α,α-dichlorotosylhydrozones under ambient conditions. This fast and efficient alternative affords exclusively 1,4-substituted triazole “click products” with complete retention of configuration. Primary amines, inherent to many natural products, can be modified in this way without protecting group manipulations.