1,3-dipolar cycloaddition reactions of 2-substituted azomethine N-oxides with N-benzyl maleimides leading to the synthesis of stereoisomers

[摘要]：The azomethine N-oxides (1) on reacting with N-benzylmaleimide (2) provide a mixture of stereoisomers 2,3-diphenyl-5-benzyl-4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6dione derivatives (3) in good yields. These isomers have been assigned cis and trans configurations (3-A and 3-B) with respect to proton C3-H on the azomethinic carbon on the basis of their PMR and H-NMR COSY data. The ratio between cis and trans isomers has been found to be dependent on substituents present at ortho position of C-phenyl aldehydic moiety. The salient feature of these 1,3-dipolar cycloaddition reactions lies in that the benzylic protons on N-benzyl moiety suffer gem coupling, indicating magnetic nonequivalence. J. Heterocyclic Chem.,, (2012).

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