Issue 24, 2005
From the journal:

Organic & Biomolecular Chemistry

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.

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

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Article information

DOI
https://doi.org/10.1039/B513397A
Article type
Paper
Submitted
21 Sep 2005
Accepted
14 Oct 2005
First published
15 Nov 2005

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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