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Synthesis of carbohydrate derived alpha methylene gamma lactones by diastereoselective low temperature reformatsky type reactions



Synthesis of carbohydrate derived alpha methylene gamma lactones by diastereoselective low temperature reformatsky type reactions



Journal of Carbohydrate Chemistry 5(3): 459-468



Hexopyranoside- and hexofuranose uloses with either ethyl 2-(bromomethyl)acrylate in the presence of laminar Zn/Ag-graphite or ethyl 2-(trimethylsilylmethyl)acrylate/tetra-n-butylammonium fluoride undergo stereoselective branching, mainly with formation of spiro .alpha.-methylene-.gamma.-lactones.

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Accession: 006567203

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