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.
Boutureira
Omar
O
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcel.lí Domingo s/n, 43007 Tarragona, Spain. omar.boutureira@urv.cat
Rodríguez
Miguel A
MA
Díaz
Yolanda
Y
Matheu
M Isabel
MI
Castillón
Sergio
S
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012643:Selenium / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
D013440:Sulfides; D013865:Thioglycosides; D012643:Selenium