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Dr. Sander S. van Berkel, Dipl.-Chem. Sebastian Brauch, Lars Gabriel, Dipl.-Chem. Michael Henze, Dipl.-Chem. Sebastian Stark, Dipl.-Chem. Dimitar Vasilev, Prof. Dr. Ludger A. Wessjohann, Dr. Muhammad Abbas and Prof. Dr. Bernhard Westermann Traceless Tosylhydrazone-Based Triazole Formation: A Metal-Free Alternative to Strain-Promoted Azide–Alkyne Cycloaddition Angewandte Chemie International Edition 51

Version of Record online: 18 APR 2012 | DOI: 10.1002/anie.201108850

Thumbnail image of graphical abstract

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.

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