Synthesis and reactivity of β-phenylselanyl α-oxoesters

Article abstract of DOI:10.1016/S0040-4020(97)10117-X

β-Phenylsetanyl α-oxoesters 2 were prepared by N-phenylselanyl morpholine 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 corrsponding selenoxides to the diethyl 3-alkylidene-2- hydroxysuccinates 7. The 2-(1-butoxycarbonylamino)-3-alkylidenesuccinates 8 were prepared in a similar way. The decomposition of halo-adducts derived from components 6 has the synthesis of the siethyl 3-alkylidene-2- halosuccinates 9 and 10.