New spiro[indeno[1,2-b]quinoxaline-11,2´-pyrrolidine] derivatives were prepared in high yield stereoselectively from an efficient multicomponent 1,3-dipolar cycloaddition reaction between ninhydrin, phenylenediamine, sarcosine, and chalcones. The regiochemistry and stereochemistry of resultant cycloadducts have been determined by several 2D NMR spectroscopic techniques and X-ray single crystal diffraction.