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| Title
| - Stereocontrolled Synthesis of α-C-Galactosamine Derivatives viaChelation-Controlled C-Glycosylation
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| Abstract
| - The samarium diiodide-promoted reduction of2-deoxy-2-acetamidogalactosyl pyridyl sulfoneα-5with ketones or aldehydes under Barbier conditions led unexpectedly tothe stereoselective synthesisof α-C-galactosamine derivatives in good yields. Withcarbonyl substrates, α:β selectivities rangedfrom 20:1 to 5:1, and with aldehydes a stereoselectivity ofapproximately 5:1 was observed at C7in favor of the S-isomer. The stereochemical preferenceof these C-glycosylation reactions isexplained by the intermediacy of an α-oriented anomeric glycosylsamarium(III) compound that isstabilized via chelation of the metal ion to the C2-acetamidogroup.
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