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

Géraldine Calvet; Régis Guillot; Nicolas Blanchard; Cyrille Kouklovsky

doi:10.1039/B513397A

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

Géraldine Calvet,^a Régis Guillot,^a Nicolas Blanchard*^a and Cyrille Kouklovsky*^a

* Corresponding authors

^a Laboratoire de Synthèse des Substances Naturelles, UMR CNRS 8615, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Batiment 410, Université Paris Sud, Orsay, France
E-mail: nblanchard@icmo.u-psud.fr, cykouklo@icmo.u-psud.fr
Fax: +33 1 69 15 46 79
Tel: +33 1 69 15 73 91

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.

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Publication details

The article was received on 21 Sep 2005, accepted on 14 Oct 2005 and first published on 15 Nov 2005

Article type: Paper

DOI: 10.1039/B513397A

Citation: Org. Biomol. Chem., 2005,3, 4395-4401

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

G. Calvet, R. Guillot, N. Blanchard and C. Kouklovsky, Org. Biomol. Chem., 2005, 3, 4395
DOI: 10.1039/B513397A
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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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