Home / Publications / Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions

Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions

Alexander Mikhailovich Genaev 1
Alexander Mikhailovich Genaev
Georgii Efimovich Salnikov 1, 2
Georgii Efimovich Salnikov
Andrey Vladimirovich Shernyukov 1
Andrey Vladimirovich Shernyukov
Zhongwei Zhu 2
Zhongwei Zhu
Konstantin Yurievich Koltunov 2, 3
Konstantin Yurievich Koltunov
Published 2017-12-22
CommunicationVolume 28, Issue 1, 27-28
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Genaev A. M. et al. Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions // Mendeleev Communications. 2017. Vol. 28. No. 1. pp. 27-28.
GOST all authors (up to 50) Copy
Genaev A. M., Salnikov G. E., Shernyukov A. V., Zhu Z., Koltunov K. Y. Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions // Mendeleev Communications. 2017. Vol. 28. No. 1. pp. 27-28.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.01.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.007
TI - Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions
T2 - Mendeleev Communications
AU - Genaev, Alexander Mikhailovich
AU - Salnikov, Georgii Efimovich
AU - Shernyukov, Andrey Vladimirovich
AU - Zhu, Zhongwei
AU - Koltunov, Konstantin Yurievich
PY - 2017
DA - 2017/12/22
PB - Mendeleev Communications
SP - 27-28
IS - 1
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Genaev,
author = {Alexander Mikhailovich Genaev and Georgii Efimovich Salnikov and Andrey Vladimirovich Shernyukov and Zhongwei Zhu and Konstantin Yurievich Koltunov},
title = {Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions},
journal = {Mendeleev Communications},
year = {2017},
volume = {28},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.007},
number = {1},
pages = {27--28},
doi = {10.1016/j.mencom.2018.01.007}
}
MLA
Cite this
MLA Copy
Genaev, Alexander Mikhailovich, et al. “Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions.” Mendeleev Communications, vol. 28, no. 1, Dec. 2017, pp. 27-28. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.007.

Abstract

Compared with the parent 1,1-bi-2-naphthol (BINOL), its dimethyl ether is highly resistant towards racemization under moderate acidic conditions. This finding confirms the hypothetical mechanism of BINOL atropisomerization including internal rotation around the C1sp3 –C1'sp3 bond in its protonatedforms.

References

2.
Developments in Chiral Binaphthyl‐Derived Brønsted/Lewis Acids and Hydrogen‐Bond‐Donor Organocatalysis
Schenker S., Zamfir A., Freund M., Tsogoeva S.B.
European Journal of Organic Chemistry, 2011
3.
BINOL:  A Versatile Chiral Reagent
Brunel J.M.
Chemical Reviews, 2005
4.
Modified BINOL Ligands in Asymmetric Catalysis
Chen Y., Yekta S., Yudin A.K.
Chemical Reviews, 2003
5.
Non-Symmetrically Substituted 1,1‘-Binaphthyls in Enantioselective Catalysis
Kočovský P., Vyskočil Š., Smrčina M.
Chemical Reviews, 2003
6.
10.1016/j.mencom.2018.01.007_sbref0005f
Pu
1 1’-Binaphthyl-Based Chiral Materials: Our Journey, 2010
7.
Host-guest complexation. 7. The binaphthyl structural unit in host compounds
Kyba E.P., Gokel G.W., De Jong F., Koga K., Sousa L.R., Siegel M.G., Kaplan L., Sogah G.D., Cram D.J.
Journal of Organic Chemistry, 1977
8.
F8BINOL, an Electronically Perturbed Version of BINOL with Remarkable Configurational Stability
Yudin A.K., Martyn L.J., Pandiaraju S., Zheng J., Lough A.
Organic Letters, 1999
9.
Static and Dynamic Properties of 1,1′-Bi-2-naphthol and Its Conjugated Acids and Bases
Alkorta I., Cancedda C., Cocinero E.J., Dávalos J.Z., Écija P., Elguero J., González J., Lesarri A., Ramos R., Reviriego F., Roussel C., Uriarte I., Vanthuyne N.
Chemistry - A European Journal, 2014
10.
Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization
Genaev A.M., Salnikov G.E., Shernyukov A.V., Zhu Z., Koltunov K.Y.
Organic Letters, 2017
11.
Koltunov K.Y., Chernov A.N.
Mendeleev Communications, 2015
12.
Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL
Gavrilov K.N., Zheglov S.V., Novikov I.M., Chuchelkin I.V., Gavrilov V.K., Lugovsky V.V., Zamilatskov I.A.
Russian Chemical Bulletin, 2015
14.
Chiral discriminations with cinchona alkaloids
Salvadori P., Pini D., Rosini C., Bertucci C., Uccello-Barretta G.
Chirality, 1992
15.
10.1016/j.mencom.2018.01.007_bib0040
Repinskaya
Russ. J. Org. Chem., 1992