Studies on the Zn(II)-mediated electrophilic selenocyclization and elimination of 3,4-O-isopropylidene-protected hydroxyalkenyl sulfides: synthesis of a 2-phenylselenenyl glycal

Herein, we describe a mild and efficient Zn(II)-mediated electrophilic selenocyclization reaction of readily available and stable 3,4-O-isopropylidene-protected hydroxyalkenyl sulfides to 2-deoxy-2-phenylselenenyl-1-thio-glycosides. This material was transformed into a 2-phenylselenenyl glycal in a controlled manner using an activation–elimination sequence.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide