The pharmaceutically significant 2,3-dihydroquinolin-4-one scaffolds were constructed diastereoselectively and facilely via redox-neutral cascade Knoevengel condensation/[1,7]-hydride transfer/cyclization/transesterification in DCE from readily available methyl 2-aminobenzoacetate and diverse aldehydes, which features novel and highly valuable product structures, diastereoselective construction of all-carbon quaternary centers carrying allylic or propargyl groups as well as a privileged 3-spirocyclic 3,4-dihydrocoumarin moiety, an unusual pattern of [1,7]-hydride transfer, broad substrate scope, etc.