Improved Dimethylzinc-Promoted Vinylation Of Nitrones With Vinylboronic Esters

Nageswaran Praveenganesh (1) , Cristina de Candia (1) , Antony Memboeuf (1) , György Lendvay , Yves Gimbert (2) , Pierre Yves Chavant (2)

1 DCM - Département de Chimie Moléculaire
2 DCM - SeRCO - Département de Chimie Moléculaire - Synthèse Et Réactivité en Chimie Organique

Vinylboronic esters derived from 4,4,6-trimethyl-[1,3,2]dioxaborinane react with nitrones in the presence of dimethylzinc; nucleophilic addition of the vinyl group onto nitrones produces N-allylic hydroxylamines in fair yields. The sequence is compatible with various functional groups on the vinylic moiety. The mechanism and kinetic aspects are discussed on the basis of DFT calculations.

Domaines: Chimie organique

Nageswaran Praveenganesh, Cristina de Candia, Antony Memboeuf, György Lendvay, Yves Gimbert, et al.. Improved Dimethylzinc-Promoted Vinylation Of Nitrones With Vinylboronic Esters. Journal of Organometallic Chemistry, 2010, 695 (22), pp.2447-2454. ⟨10.1016/j.jorganchem.2010.07.009⟩. ⟨hal-00532662⟩