C(2) chiral-4-chromanones have attracted considerable attention owing to their pronounced biological activities. The asymmetric synthesis of C(2) chiral-4-chromanone derivatives has therefore emerged as an important research topic in the field of organic synthesis. Among the various strategies, the use of chromenone as the substrate to obtain C(2) chiral-4-chro- manone derivatives through asymmetric addition of C(2)=C(3) double bond has become one of the main routes for the synthesis of such derivatives due to the advantages of ready availability of the substrates, high stereoselectivity, and excellent atom economy. The synthetic methodology over the past decade is summarized with a focus on asymmetric catalysis mediated by chiral metal complexes. A comparative analysis of the stereoselective mechanisms under different catalytic systems is provided, the structural features of catalytic systems that are beneficial for enhancing stereoselectivity are summarized, and the current challenges and future perspectives in this field are discussed.

Key words: biological activity, chromenone, asymmetric synthesis, chiral metal complex, chromanone