Intramolecular aminochalcogenation and diamination of alkenes employing N-iodosuccinimide

A NIS-mediated intramolecular diamination and aminosulfuration of alkenes with N-alkyl or N-aryl thioureas is reported. A chiral cyclic thiourea was also synthesized by the methodology. The protocol is also proven to be efficient in the intramolecular diamination and/or aminooxygenation of alkenes with N-alkyl or N-aryl ureas and ones with N-carbamate sulfamides. The resulting bicyclic thiourea could be further transformed into bicyclic guanidine. (C) 2015 Elsevier Ltd. All rights reserved.