Oxidative reactions of sulfinyl dienes as an entry to functionalized carbohydrate-like products and furans
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Add time:08/22/2019 Source:sciencedirect.com
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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