Intermolecular nitroso Diels-Alder cycloaddition of alpha-acetoxynitroso derivatives in aqueous medium
Géraldine Calvet1, Régis Guillot, Nicolas Blanchard
1Laboratoire de Synthèse des Substances Naturelles, UMR CNRS 8615, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Batiment 410, Université Paris Sud, 91400, Orsay, France. nblanchard@icmo.u-psud.fr, cykouklo@icmo.u-psud.fr.
Abstract:
The Diels-Alder cycloadditions of the alpha-acetoxynitroso dienophile in water are reported. The rapid and high yielding synthesis of structurally diverse 3,6-dihydro-1,2-oxazines complements the straightforward elaboration of aminoalcohols obtained from the alpha-acetoxynitroso derivative in anhydrous medium. A rationale for this solvent-dependent product distribution is proposed.
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