A highly diastereoselective synthesis of functionalized trans gem-difluorocyclopropane carboxylate 3 was achieved through sequential Michael addition of lithium enolate of homochiral N-acylimidazolidinone 2 with 2,4,6-trimethylphenyl (TMP) 4-bromo-4,4-difluorocrotonate 1 and triethylborane-mediated intramolecular substitution reaction.