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- W2102431569 abstract "The anion [(EtO)2P(O)CFCO2Et]−Li+, pregenerated from its precursor diethyl (carboethoxyfluoromethyl)phosphonate (EtO)2P(O)CFHCO2Et and n-butyllithium, was added via syringe to a THF solution of ethyl oxaiyl chloride to yield an acylated phosphonate (EtO)2P(O)CF(COCO2Et)CO2Et. In situ reaction with Grignard reagents RMgX produces the α-fluorodiesters (E,Z)-R(CO2Et)C=CFCO2Et in good yields. In contrast, addition of ethyl oxalyl chloride to a THF solution of diethyl (carboethoxyfluoromethyl)phosphonate anion gives an isolated intermediate (EtO)2P(O)CFCO2Et(CO2Et)C=CFCO2Et. Subsequent reaction of this isolated intermediate with Grignard reagents also affords a one-pot synthesis of the α-fluorodiesters with high E-stereoselectivity. The E-stereoselectivity increases when HMPT or DMPU is used as a cosolvent in the preparation of diethyl 2-fluoro-3-phenylfumarate (E,Z)-Ph(CO2Et)C=CFCO2Et." @default.
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- W2102431569 date "1998-08-01" @default.
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- W2102431569 title "Isolation and Characterization of intermediate in the Synthesis of α-Fluorodiesters" @default.
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- W2102431569 doi "https://doi.org/10.1002/jccs.199800082" @default.
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