Oxidative reactions of sulfinyl dienes as an entry to functionalized carbohydrate-like products and furans |
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Authors: | Alejandro Castellanos Iñaki Osante Jorge Fernández Roberto Fernández de la Pradilla Alma Viso |
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Affiliation: | Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid Spain |
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Abstract: | Oxidative cleavage (OsO4/NaIO4) of a monoprotected dihydroxy sulfinyl diene affords a lactol, readily transformed into a sulfinyl pyranose. Alternatively, base promoted intramolecular cyclization of a lactol derived carbamate to a bicyclic oxazolidinone followed by simple transformations leads to an amino sulfonyl pyranose. In contrast, ozonolysis of a variety of hydroxy sulfinyl dienes leads to fair yields of 3-sulfinyl furans in a single step. |
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Keywords: | Corresponding author. Sulfoxides Pyranoses Furans Oxidation Sulfones |
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