An organocatalytic highly enantioselective Michael-aldol cascade access to valuable chiral dihydronaphthalenes has been realized. Notably, the strategy via activation of nucleophilic alkyl chains by introducing nitro, chloro, or CF3 group(s) at the ortho- and/or para-position(s) on an aromatic ring renders them readily deprotonated to produce highly reactive nulecophilic species in the cascade process under mild conditions.