A series of C2-symmetrical chiral 2,5-bis(4'-alkyloxazolin-2-yl) thiophenes (thiobox) have been synthesized from thiophene-2, 5-dicarboxylic acid by sequential amidation with a chiral ethanolamine, conversion of hydroxyl to chloro group,and base-promoted oxazoline ring formation. As demonstrated by ( - )-2, 5-bis [ 4'-( S)-isopropyloxazolin-2'-yl] thiophene,these thiobox systems exhibited remarkable chirality recognition of 1, 1'-bi-2-naphthol giving rise to pronounced shifts in the 1H NMR signals of the latter axial chiral compound at the positions of C-3, C-4, C-5, and C-8.