Addition Reactions of Benzenesulfinic Acid with Glycals and 1,2-Dibromosugars |
| |
| Authors: | Vikram Basava Broc Flores Matthew Giovine Thomas Licisyn Katelyn Walck Walter Boyko |
| |
| Institution: | Department of Chemistry , Villanova University , Villanova, PA, 19085, USA |
| |
| Abstract: | The addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave sulfinate esters as products by reaction at oxygen rather than at sulfur. The sulfinate esters were obtained as mixtures of stereoisomers at the stereogenic sulfur atom. Trapping of the sulfinates with carboxylate nucleophiles was observed during attempted oxidation with MCPBA. |
| |
| Keywords: | Benzenesulfinic acid glycosyl phenylsulfones carbohydrate sulfinate esters |
|
|
