Synlett 2018; 29(16): 2167-2170
DOI: 10.1055/s-0037-1610635
cluster
© Georg Thieme Verlag Stuttgart · New York

A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis

Yuuya Nagata*
a  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan   eMail: nagata@sbchem.kyoto-u.ac.jp   eMail: suginome@sbchem.kyoto-u.ac.jp
,
Yasuo Shimada
b  Graduate School of Natural Science and Technology Kanazawa University, Kakuma-machi, Kanazawa 920–1192, Japan   eMail: ogoshi@se.kanazawa-u.ac.jp
,
Tsuyoshi Nishikawa
a  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan   eMail: nagata@sbchem.kyoto-u.ac.jp   eMail: suginome@sbchem.kyoto-u.ac.jp
,
Ryohei Takeda
a  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan   eMail: nagata@sbchem.kyoto-u.ac.jp   eMail: suginome@sbchem.kyoto-u.ac.jp
,
Makoto Uno
a  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan   eMail: nagata@sbchem.kyoto-u.ac.jp   eMail: suginome@sbchem.kyoto-u.ac.jp
,
Tomoki Ogoshi*
b  Graduate School of Natural Science and Technology Kanazawa University, Kakuma-machi, Kanazawa 920–1192, Japan   eMail: ogoshi@se.kanazawa-u.ac.jp
c  WPI Nano Life Science Institute (NanoLSI), Kanazawa University, Kakuma-machi, Kanazawa, 920–1192, Japan
,
Michinori Suginome*
a  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan   eMail: nagata@sbchem.kyoto-u.ac.jp   eMail: suginome@sbchem.kyoto-u.ac.jp
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This work was partially supported by the following grants-in-aid: Grant-in-Aid for Scientific Research on Innovative Areas: π-System Figuration (JP15H00990 and JP17H05148; TO), (JP15H00994, YN), Coordination Asymmetry (JP17H05368, YN), Soft Crystal (JP18H04510, TO), and Kiban B (JP16H04130, TO) from MEXT Japan, as well as JST PRESTO (JPMJPR1313, TO), JST CREST (JPMJCR14L1, SM), and a Kanazawa University Chozen Project. NanoLSI is supported by the World Premier International (WPI) Research Center Initiative, Japan.
Weitere Informationen

Publikationsverlauf

Received: 12. Juli 2018

Accepted after revision: 13. August 2018

Publikationsdatum:
24. August 2018 (online)


Published as part of the Cluster Atropisomerism – in Memoriam Kurt Mislow

Abstract

A planar-chiral pillar[5]arene with cyclohexylmethoxy side chains and a pendant diphenylphosphine was prepared and used as a chiral ligand in asymmetric reactions. Chirality transfer from the planar-chiral pillar[5]arene scaffold to the chiral biaryl moiety was demonstrated by circular dichroism (CD) spectroscopy, single-crystal X-ray diffraction analysis, and asymmetric catalysis.

Supporting Information

 
  • References and Notes

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