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An chiral RhII‐catalyzed cyclooligomerization reaction of thiophenes having triazolyl and vinyl substituents at the 2‐ and 4‐positions was studied. Structurally interesting cyclic trimers, having chirality that is ascribed only to the orientation of the 2,4‐disubstituted thiophene rings, are obtained. The 2,4‐disubstitution of the starting thiophene monomer allows production of each of the enantiomers. The observed electronic circular‐dichroism spectra are in accord with those simulated by density‐functional theory calculations. [ABSTRACT FROM AUTHOR]

An asymmetric synthesis of C3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C3-symmetric triangular macrocycle motif. This method can be applied to the synthesis of an enantiopure hydrocarbon, which owes its chirality to asymmetric distribution of H/D atoms on the benzene rings. [ABSTRACT FROM AUTHOR]