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- W2045488462 abstract "Optically pure sulfinylfuranones undergo oxidation at sulfur followed by a totally stereoselective epoxidation at the electron deficient double bond by treatment with MCPBA at room temperature to afford, in good yields, enantiomerically pure 4-ethoxy-5-alkyl-1-p-tolylsulfonyl-3,6-dioxabicyclo[3.1.0]hexan-2-ones. These epoxyfuranones are obtained along with cyclopropanefuranones by reaction of 4-ethoxy-6-p-tolylsulfinylfuro[3,4-c]pyrazolin-6-ones with MPCBA. In both cases, the formation of the sulfonyl epoxylactones takes place by oxidation of the sulfonylfuran-2(5H)-one resulting from the starting materials. This reaction is completely stereoselective (controlled by the configuration of C-5 of furanone) and results from the nucleophilic attack of the peroxycarboxylate generated by interaction of the reagent with weak basic centres at the substrates." @default.
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- W2045488462 date "2010-01-01" @default.
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- W2045488462 title "Asymmetric synthesis of 4-ethoxy-1-p-tolylsulfonyl-3,6-dioxabicyclo[3.1.0]hexan-2-ones" @default.
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- W2045488462 doi "https://doi.org/10.1016/j.tet.2009.10.106" @default.
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