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Paper | Regular issue | Vol 78, No. 8, 2009, pp.1977-1991
Published online, 13th April, 2009
DOI: 10.3987/COM-09-11681
Reactivity of Arylnitrile Oxides and C-Aroyl-N-phenylnitrones with 3-Methylenedihydro-(3H)-furan-2-one and Itaconic Anhydride

Christophe Roussel, Kabula Ciamala,* Joël Vebrel, and Claude Riche

*Institute of UTINAM UMR CNRS 6213, Faculty of Science and Technology, University of Franche-Comté, 16 Route de Gray, F-25030 Besançon, France

Abstract

1,3-dipolar cycloaddition is a powerful route for the synthesis of five-membered heterocycles. The [3+2] cycloadditions of some α-methylene-γ-buryrolactones, namely 3 methylenedihydro-(3H)-furan-2-one (1) and itaconic anhydride (2) were studied. Their reactions with arylnitrile oxides (3) and C-aroyl-N-phenylnitrones (7) proceed with complete regioselectivity. From a stereochemical point of view, the addition of arylnitrile oxides (3) leads to the unique spiroheterocycles (4-5). Actually, a single stereocenter is generated during the reaction. In the particular case of p-nitrophenylnitrile oxide (3d), only the diacidic form (10d) of the spiroheterocyle (5d) was isolated. In contrast, the addition of C-aroyl-N-phenylnitrones (7) produces a couple of diastereoisomers, since two stereocenters are generated simultaneously. Nevertheless, the reaction is regioselective and stereospecific leading also to the single spiroheterocycles (19-20). The proposed stereochemistry of spiranic compounds (19d) and (20d) has been corroborated by two single crystal X-ray crystallographic analysis.