Alain Gadras

Direct regiospecific allylic amination via silicon induced pericyclic reactions : A novel synthesis of gamma vinyl gaba

Abstract Silylation of the product of the ene reaction of N -sulphinylbenzene sulphonamide and an alkene induces a [2,3]sigmatropic rearrangement, leading to an allylamine derivative. The reaction is used in a synthesis of γ-vinyl GABA.

A novel and efficient arylation of malononitrile catalyzed by nickel(0) complexes

Abstract We report the first use of a nickel catalyst for the direct arylation of a β-difunctionalized compound, the malononitrile, from halogenated aromatic substrates. The catalytic system is quite simple: Ni(PPh3)3, generated in situ from NiBr2(PPh3)2, PPh3 and zinc. Good yields and excellent selectivities have been obtained in α-arylmalononitriles from iodobenzene, but also from bromo- or chloro-aromatic substrates.

Alkylation selective sur l'azote le moins nucleophile de para-aminoarylsulfonamides

Abstract N-sulfinyl derivatives of sulfamides give selective ene reactions involving the sulfonamide function. The formed ene adducts react with hexamethyldisilazane to afford original sulfamides resulting from allylation on the less nucleophilic nitrogen atom.

A new ene reaction mediated access to cycloheptatriene enol thio-ethers

Abstract The sequence, ene reaction with N-sulfinylbenzene sulfonamides, treatment with reductive Grignard reagents has been shown, when performed on Δ 3 -carene, to be a straightforward synthetic approach towards functionalized cycloheptatrienic enol thio-ethers.

TWO STEP SYNTHESIS OF 3,7,7-TRIMETHYL-1,3,5-CYCLOHEPTATRIENE FROM Δ3-CARENE

Abstract 3,7,7-trimethyl-1,3,5-cycloheptatriene was obtained in 74% overall yield when adducts from ene reaction between Δ3-carene and N-sulphinyl arenesulphonamides are reacted with hexamethyl disilazane at 80°C.