^a Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China
^b School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

A new class of bis-spiroisoxazolines were prepared in moderate to good yields in a highly regioselective cycloaddition of nitrile oxide with bis(arylmethylidene)cycloalkanone. The structures of the products were characterized thoroughly by IR, elemental analysis, NMR together with X-ray crystallographic analysis. The result of crystal diffraction indicates that this 1,3-dipolar cycloaddition has high regioselectivity. The density functional calculations provide a reasonable explanation on the regioselectivity for the cycloaddition reaction.