Tetrahedron p. 16767 - 16782 (1997)
Update date:2022-07-30
Topics:
Boivin, Stephane
Outurquin, Francis
Paulmier, Claude
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.
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