Organic Letters
Letter
various amines with trityl chloride. Previously, the asymmetric
inductions in the anion-binding helical structures of dipyrro-
lyldiketone boron complexes were achieved by chiral anion
(5) (a) Maeda, H.; Bando, Y.; Shimomura, K.; Yamada, I.; Naito, M.;
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(c) Haketa, Y.; Bando, Y.; Takaishi, K.; Uchiyama, M.; Muranaka, A.;
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recognition and ion pairing with chiral cations. Thus, by the
modifications of core structures and introduction of appropriate
substituents, dipyrrolyldiketone boron complexes are expected
to be applicable to the chiral hydrogen-bonding catalysts. We
are currently investigating further applications in hydrogen-
bonding catalysis, as well as the development of asymmetric
ion-directed catalysis via the use of chiral anion complexes and
ion pairs.
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012, 51, 7967. (d) Maeda, H.; Shirai, T.; Bando, Y.; Takaishi, K.;
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Mizuno, N.; Araoka, F.; Takezoe, H.; Maeda, H. Angew. Chem., Int. Ed.
2
010, 49, 10079. (b) Haketa, Y.; Honsho, Y.; Seki, S.; Maeda, H.
Chem. - Eur. J. 2012, 18, 7016. (c) Dong, B.; Sakurai, T.; Honsho, Y.;
Seki, S.; Maeda, H. J. Am. Chem. Soc. 2013, 135, 1284. (d) Dong, B.;
Sakurai, T.; Bando, Y.; Seki, S.; Takaishi, K.; Uchiyama, M.; Muranaka,
A.; Maeda, H. J. Am. Chem. Soc. 2013, 135, 14797. (e) Yamakado, R.;
Sakurai, T.; Matsuda, W.; Seki, S.; Yasuda, N.; Akine, S.; Maeda, H.
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ASSOCIATED CONTENT
Supporting Information
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S
(7) Cafeo, G.; De Rosa, M.; Kohnke, F. H.; Neri, P.; Soriente, A.;
Experimental procedures and detailed characterization
data for the compounds (PDF)
Valenti, L. Tetrahedron Lett. 2008, 49, 153.
(8) Roucan, M.; Kielmann, M.; Connon, S. J.; Bernhard, S. S. R.;
Senge, M. O. Chem. Commun. 2018, 54, 26.
(
9) (a) Taylor, M. S.; Tokunaga, N.; Jacobsen, E. N. Angew. Chem.,
AUTHOR INFORMATION
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Int. Ed. 2005, 44, 6700. (b) Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J.
Am. Chem. Soc. 2007, 129, 6686.
(10) (a) Schafer, A. G.; Wieting, J. M.; Fisher, T. J.; Mattson, A. E.
Angew. Chem., Int. Ed. 2013, 52, 11321. (b) Hardman-Baldwin, A. M.;
Visco, M. D.; Wieting, J. M.; Stern, C.; Kondo, S.; Mattson, A. E. Org.
Lett. 2016, 18, 3766.
ORCID
Notes
(11) (a) Zurro, M.; Asmus, S.; Beckendorf, S.; Mu
̈
ck-Lichtenfeld, C.;
Mancheno, O. G. J. Am. Chem. Soc. 2014, 136, 13999. (b) Mancheno,
̃
̃
O. G.; Asmus, S.; Zurro, M.; Fischer, T. Angew. Chem., Int. Ed. 2015,
4, 8823. (c) Fischer, T.; Bamberger, J.; Mancheno, O. G. Org. Biomol.
Chem. 2016, 14, 5794. (d) Zurro, M.; Asmus, S.; Bamberger, J.;
Beckendorf, S.; Mancheno, O. G. Chem. - Eur. J. 2016, 22, 3785.
(e) Fischer, T.; Duong, Q.-N. N.; Mancheno, O. G. Chem. - Eur. J.
2017, 23, 5983.
12) Compared with the binding with Cl as a tetrabutylammonium
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
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This work was supported by JSPS KAKENHI Grant Numbers
JP26288042 and JP18H01968 for Scientific Research (B) and
JP26107007 for Scientific Research on Innovation Areas
̃
−
(
−
salt (ref 4b), the binding with Cl as the salt of the N-acylquinolinium
cation was less effective probably due to the more tightly bound ion
“Photosynergetics” and Ritsumeikan Global Innovation Re-
search Organization (R-GIRO) Project (2017−2022). The-
oretical calculations were partially performed at Research
Center for Computational Science, Okazaki, Japan. We thank
Prof. Hikaru Takaya, Kyoto University, for Fourier transform
ion cyclotron resonance (FT-ICR) mass spectrometries and
Prof. Hitoshi Tamiaki, Ritsumeikan University, for various
measurements.
−
pair of Cl and the cation.
(
13) (a) Brown, A. R.; Kuo, W.-H.; Jacobsen, E. N. J. Am. Chem. Soc.
010, 132, 9286. (b) Padmanaban, M.; Biju, A. T.; Glorius, F. Org.
Lett. 2011, 13, 98.
14) Beckendorf, S.; Asmus, S.; Lichtenfeld, C.; Manchen
Chem. - Eur. J. 2013, 19, 1581.
2
(
̃
o, O. G.
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