TY - JOUR
T1 - Synthesis, Structure, and Dynamics of Chiral Eight-Membered Cyclic Molecules with Thienylene and Cyclopropylene Units Alternately Connected
AU - Miura, Tomoya
AU - Ishihara, Yumi
AU - Nakamuro, Takayuki
AU - Moritani, Shunsuke
AU - Nagata, Yuuya
AU - Murakami, Masahiro
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI [Grants-in-Aid for Scientific Research (B) (20H02739) (T.M.), 21H01924 (Y.N.)], JST-ERATO (JPMJER1903) (Y.N.), JSPS-WPI (Y.N.) and the Asahi Glass Foundation (T.M.). T.N. acknowledges JSPS fellowship for young scientists. We thank Dr. T. Fujihara and Dr. T. Hirose (Kyoto University) for their kind help in X-ray and ECD analyses, respectively.
Funding Information:
This work was supported in part by JSPS KAKENHI [Grants‐in‐Aid for Scientific Research (B) (20H02739) (T.M.), 21H01924 (Y.N.)], JST‐ERATO (JPMJER1903) (Y.N.), JSPS‐WPI (Y.N.) and the Asahi Glass Foundation (T.M.). T.N. acknowledges JSPS fellowship for young scientists. We thank Dr. T. Fujihara and Dr. T. Hirose (Kyoto University) for their kind help in X‐ray and ECD analyses, respectively.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/2/21
Y1 - 2022/2/21
N2 - 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.
AB - 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.
KW - asymmetric synthesis
KW - chirality
KW - conformation analysis
KW - rhodium
KW - structure elucidation
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U2 - 10.1002/chem.202103962
DO - 10.1002/chem.202103962
M3 - Article
C2 - 34928539
AN - SCOPUS:85122910244
SN - 0947-6539
VL - 28
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 10
M1 - e202103962
ER -