Síntese de calcogenoéteres e 3-fenilcalcogenilpropan-1,2-dióis enantiomericamente puros

Abstract

In this work, we developed a methodology to obtain asymmetric chalcogenoethers 3 through the substitution reaction of nucleophilic species of chalcogen (S, Se and Te), generated in situ from the corresponding diorganoil dichalcogenides 1 with (R)- or (S)-tosyl solketal 2. The corresponding chalcogenoethers 3 were obtained in pre-established conditions in previous studies, using sodium borohydride as a reducing agent and polyethylene glycol- 400 (PEG-400) as solvent at 50 ºC under conventional heating. This methodology allowed the synthesis of 16 compounds with good yield (63-88%) and short reaction times. Subsequently, some of (R)- or (S)-chalcogenoethers 3 were treated with an alcoholic solution of the acidic cation exchange resin Dowex-(H+)®, leading to the formation of respective 3- phenylchalcogenylpropane-1,2-diols 4 in excellent yield (85-91%) and short reaction times.