Tetrahedron

Synthesis and reactivity of β-phenylselanyl α-oxoesters

S Boivin, F Outurquin, C Paulmier

Index: Boivin, Stephane; Outurquin, Francis; Paulmier, Claude Tetrahedron, 1997 , vol. 53, # 49 p. 16767 - 16782

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Citation Number: 15

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 ...