Enantioselective Syntheses of 2-Deoxyxylono-1, 4-lactone and 2-Deoxyribono-1, 4-lactone from 1, 3-Dioxan-5-yl Diazoacetates

…, JS Tedrow, AB Dyatkin, CJ Spaans…

Index: Doyle, Michael P.; Tedrow, Jason S.; Dyatkin, Alexey B.; Spaans, Coenraad J.; Ene, Doina G. Journal of Organic Chemistry, 1999 , vol. 64, # 24 p. 8907 - 8915

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Citation Number: 44

Abstract

1, 3-Dioxan-5-yl diazoacetates are valuable substrates for highly diastereoselective and enantioselective carbon-hydrogen insertion reactions. trans-2-(tert-Butyl)-1, 3-dioxan-5-yl diazoacetate is a direct precursor to 2-deoxyribono-1, 4-lactone in up to 81% ee, whereas cis-2-(tert-butyl)-1, 3-dioxan-5-yl diazoacetate yields only the protected 2-deoxyxylono-1, 4- lactone in up to 96% ee. However, trans-2-aryl-1, 3-dioxan-5-yl diazoacetate (aryl= phenyl ...

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