Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 10, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103962
Keywords
asymmetric synthesis; chirality; conformation analysis; rhodium; structure elucidation
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Funding
- JSPS KAKENHI [20H02739, 21H01924]
- JST-ERATO [JPMJER1903]
- JSPS-WPI
- Asahi Glass Foundation
- JSPS fellowship for young scientists
- Grants-in-Aid for Scientific Research [21H01924, 20H02739] Funding Source: KAKEN
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This study investigates the asymmetric cyclooligomerization of bifunctional monomers catalyzed by rhodium(II). The major products obtained are cyclic dimers with unique structures, and it is observed that these structures can undergo ring-flipping.
A rhodium(II)-catalyzed asymmetric cyclooligomerization of bifunctional monomers possessing triazolyl and vinyl groups at 2,3- and 3,4-positions on the thiophene ring is studied. Structurally interesting cyclic dimers in which thienylene and cyclopropylene units are alternately connected are obtained as the major components. The eight-membered rings in the center are non-planar and adopt a tub-shaped conformation. We also observe the phenomenon of racemization caused by a tub-to-tub ring-flipping, the activation energy of which is determined as 108 kJ mol(-1) by electronic circular dichroism spectra measurement.
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