Abstract
β-Phenylselanyl α-oxoesters 2 were prepared by N-phenylselanyl morpholme treatment of α-oxoesters 1, oxidized into β-unsaturated α-oxoesters 5 and subjected to the Wittig-Horner olefination. The diethyl (l-phenylselanylalkyl)maleates 6 have led, after [2,3]sigmatropic rearrangement of the corresponding selenoxides, to the diethyl 3-alkylidene-2-hydroxysuccinates 7. The 2-(t-butoxycarbonylamino)-3-alkylidenesuccinates 8 were prepared in a similar way. The decomposition of halo-adducts derived from compounds 6 has allowed the synthesis of the diethyl 3-alkylidene-2-halosuccinates 9 and 10.
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