It was found that the reaction of dimethyl 2-(4chlorophenyl)cyclopropane-1,1-dicarboxylate 1a with 2 equiv. 4chlorobenzaldehyde and 2 equiv. TaCl 5 in 1,2-dichloroethane solution at 23 °C for 24 h leads to the selective formation of trichloro-substituted 4-phenyl-3,4-dihydronaphthalene-2,2(1H)dicarboxylate 2a in 89% yield (Scheme 3). The transformation of DAC 1b, which has an ethyl substituent in the ester group, occurs equally effectively under the action of 4-bromobenzaldehyde. Thus, the presence of a chlorine atom in the para position in the phenyl substituent of 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate does not prevent the reaction of DAC with a halogenated aromatic aldehyde. The use of diethyl 2-(4-chlorophenyl)cyclopropane-1,1dicarboxylate also does not prevent the conversion of DAC under the action of aromatic aldehyde and TaCl 5 . The results obtained indicate a wide range of possibilities for the application of the TaCl 5mediated reaction between 2-phenylcyclopropane-1,1dicarboxylate and aromatic aldehydes in the synthesis of functionalized tetrahydronaphthalenes.