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Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis

Vladislav Konstantinovich Gavrilov 1
Vladislav Konstantinovich Gavrilov
, 
Ilya Valer'evich Chuchelkin 1
Ilya Valer'evich Chuchelkin
, 
Sergey Viktorovich Zheglov 1
Sergey Viktorovich Zheglov
, 
Ilya Dmitrievich Firsin 1
Ilya Dmitrievich Firsin
, 
Alexei Aleksandrovich Shiryaev 1
Alexei Aleksandrovich Shiryaev
, 
Konstantin Nikolaevich Gavrilov 1
Konstantin Nikolaevich Gavrilov
, 
Alexander Vital'evich Maximychev 2
Alexander Vital'evich Maximychev
, 
Alexander Maksimovich Perepukhov 2
Alexander Maksimovich Perepukhov
, 
Nataliya Sergeevna Goulioukina 3, 4
Nataliya Sergeevna Goulioukina
, 
Irina Petrovna Beletskaya 3, 4
Irina Petrovna Beletskaya
10.1016/j.mencom.2019.01.010
Published 2018-12-28
Communication , Volume 29, Issue 1, 35-37
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Gavrilov V. K. et al. Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 35-37.
GOST all authors (up to 50) Copy
Gavrilov V. K., Chuchelkin I. V., Zheglov S. V., Firsin I. D., Shiryaev A. A., Gavrilov K. N., Maximychev A. V., Perepukhov A. M., Goulioukina N. S., Beletskaya I. P. Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 35-37.
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TY - JOUR
DO - 10.1016/j.mencom.2019.01.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.010
TI - Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis
T2 - Mendeleev Communications
AU - Gavrilov, Vladislav Konstantinovich
AU - Chuchelkin, Ilya Valer'evich
AU - Zheglov, Sergey Viktorovich
AU - Firsin, Ilya Dmitrievich
AU - Shiryaev, Alexei Aleksandrovich
AU - Gavrilov, Konstantin Nikolaevich
AU - Maximychev, Alexander Vital'evich
AU - Perepukhov, Alexander Maksimovich
AU - Goulioukina, Nataliya Sergeevna
AU - Beletskaya, Irina Petrovna
PY - 2018
DA - 2018/12/28
PB - Mendeleev Communications
SP - 35-37
IS - 1
VL - 29
ER -
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@article{2018_Gavrilov,
author = {Vladislav Konstantinovich Gavrilov and Ilya Valer'evich Chuchelkin and Sergey Viktorovich Zheglov and Ilya Dmitrievich Firsin and Alexei Aleksandrovich Shiryaev and Konstantin Nikolaevich Gavrilov and Alexander Vital'evich Maximychev and Alexander Maksimovich Perepukhov and Nataliya Sergeevna Goulioukina and Irina Petrovna Beletskaya},
title = {Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.010},
number = {1},
pages = {35--37},
doi = {10.1016/j.mencom.2019.01.010}
}
MLA
Cite this
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Gavrilov, Vladislav Konstantinovich, et al. “Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis.” Mendeleev Communications, vol. 29, no. 1, Dec. 2018, pp. 35-37. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.010.

Abstract

A P*-chiral diamidophosphite ligand of the 1,3,2-diazaphospholidine series was obtained by direct phosphorylation of N-[(1R,2R)-2-(tert-butoxycarbonylaminocyclohexyl)]-N′-[(1R)-1-(hydroxymethyl)propyl]oxalamide. The use of this ligand made it possible to reach 98% ee in the Pd-catalyzed allylation involving (E)-1,3-diphenylallyl acetate, 81% ee in the allylation of ethyl 2-oxocyclohexane-1-carboxylate with cinnamyl acetate, 78% ee in the Rh-catalyzed hydrogenation of methyl (Z)-2-acetamido-3-phenylacrylate, and 32% ee in the Rh- and Ir-catalyzed hydrosilylation of (E)-N-(4-methoxyphenyl)-1-phenylethan-1-imine with diphenylsilane. The above mentioned oxalamide provides up to 50% ee in the organocatalytic reduction of the same imine.

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