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Chiral Macrocycles Having C 3 Symmetry Resulting from Orientation of Thiophene Rings
Author(s) -
Miura Tomoya,
Nakamuro Takayuki,
Ishihara Yumi,
Nagata Yuuya,
Murakami Masahiro
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009781
Subject(s) - thiophene , chirality (physics) , enantiomer , chemistry , monomer , density functional theory , circular dichroism , crystallography , axial chirality , computational chemistry , catalysis , orientation (vector space) , stereochemistry , enantioselective synthesis , chiral symmetry breaking , organic chemistry , symmetry breaking , polymer , physics , geometry , quantum mechanics , mathematics , nambu–jona lasinio model
An chiral Rh II ‐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.