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.
Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide–Alkyne Cycloaddition†
Article first published online: 18 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 22, pages 5343–5346, May 29, 2012
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
- Issue published online: 23 MAY 2012
- Article first published online: 18 APR 2012
- WGL-PFI project
- 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.