Intermolecular nitroso Diels–Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium

…, R Guillot, N Blanchard, C Kouklovsky

Index: Calvet, Geraldine; Guillot, Regis; Blanchard, Nicolas; Kouklovsky, Cyrille Organic and Biomolecular Chemistry, 2005 , vol. 3, # 24 p. 4395 - 4401

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Citation Number: 29

Abstract

The Diels–Alder cycloadditions of the α-acetoxynitroso dienophile 1 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 α- acetoxynitroso derivative 1 in anhydrous medium. A rationale for this solvent-dependent product distribution is proposed.