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. 2020 Nov 9;59(46):20475-20479.
doi: 10.1002/anie.202009781. Epub 2020 Sep 15.

Chiral Macrocycles Having C3 Symmetry Resulting from Orientation of Thiophene Rings

Tomoya Miura  1 , Takayuki Nakamuro  1   2 , Yumi Ishihara  1 , Yuuya Nagata  1   3 , Masahiro Murakami  1
Affiliations

Chiral Macrocycles Having C3 Symmetry Resulting from Orientation of Thiophene Rings

Tomoya Miura et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: asymmetric synthesis; chirality; heterocycles; macrocycles; rhodium.

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References

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