Intermolecular nitroso Diels-Alder cycloaddition of alpha-acetoxynitroso derivatives in aqueous medium.
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.
Calvet
Géraldine
G
Laboratoire 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.
Guillot
Régis
R
Blanchard
Nicolas
N
Kouklovsky
Cyrille
C