The reactions of [2 + 3] cycloaddition of nitrile oxides to mono- and 1,2-disubstituted germylalkenes proceed regioselectively and resulted 5-Ge-substituted isoxazolines-2 from triethylvinyl- and triethylallylgermane and 4-Ge-isomers from β-triorganylgermylstyrene and ethyl triorganylgermylacrylates. In the latter case the reaction occurs stereospecifically: Z-germylalkenes give cis-, while E-germylalkenes yield trans-4,5-substituted isoxazolines. The structure of products obtained was determined by 1 H-NMR spectroscopy and for 11a confirmed by single-crystal X-ray analysis.