Expeditious synthesis of β-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent |
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| Authors: | Elena Cabianca Fabrizio Fabris Patrick Rollin |
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| Institution: | a Institut de Chimie Organique et Analytique, associé au CNRS, Université d’Orléans, B.P. 6759, F-45067 Orléans, France
b Dipartimento di Chimica, Universita Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy |
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| Abstract: | In similarity with the strongly electrophilic BPSEs and despite its more electron-rich character, 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) reacts with nucleophiles with displacement of the phenylthio moiety. Specifically it reacts with diols under basic conditions to produce β-cycloacetalic sulfoxides. The reaction has been amply developed in carbohydrate chemistry. |
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| Keywords: | Cyclic acetals Carbohydrates Sulfoxides Protecting groups |
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