3-Methyleneindolinone derivatives are important structural motifs found in many compounds of natural occurrence and pharmacological significance. However, despite their wide importance, mild and highly efficient stereoselective synthesis of (E)- and (Z)-3-methyleneindolinones still remains to be a difficult problem. Therefore, the development of new synthetic methods for their stereocontrolled preparation is of prime importance in organic synthesis. In this mini review, we highlight the advances in stereoselective synthesis of mono- and disubstituted-3-methyleneindolinones through metal-catalyzed intramolecular cyclization of N-arylpropiolamides from 1988 to 2017.