Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters |
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| Authors: | Nageswaran PraveenGanesh Antony Memboeuf Yves Gimbert |
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| Affiliation: | a Département de Chimie Moléculaire, UMR 5250-ICMG FR2607, CNRS-Université Joseph Fourier BP 53, 38041 Grenoble cedex 9, France
b Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, P.O. Box 17, H-1525, Budapest, Hungary |
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| Abstract: | 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. |
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| Keywords: | Vinylboronates Allyl-hydroxylamines Transmetallation Boron Zinc |
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