Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
| |
Authors: | Jrmy Merad Jn Matyaovský Tobias Stopka Bogdan R Brutiu Alexandre Pinto Martina Drescher Nuno Maulide |
| |
Institution: | Department of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna Austria.; Univ. Lyon, Université Claude Bernard Lyon 1, CNRS CPE Lyon, INSA Lyon, ICBMS, UMR 5246 Bât. Lederer, 1 rue Victor Grignard, 69622 Villeurbanne France |
| |
Abstract: | Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides access to multiple analogues of biologically relevant molecules. Performed experiments give insight into the reaction mechanism.A simple and scalable method for stereoselective synthesis of thioethers directly from alcohols using isothiouronium salts is presented. The utility of this thiol-free reaction was exemplified by late-stage modification of complex molecules. |
| |
Keywords: | |
|
|