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TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions

Konstantin Nikolaevich Gavrilov 1
Konstantin Nikolaevich Gavrilov
, 
Ilya Valer'evich Chuchelkin 1
Ilya Valer'evich Chuchelkin
, 
Alexei Aleksandrovich Shiryaev 2, 3
Alexei Aleksandrovich Shiryaev
, 
Ilya Dmitrievich Firsin 1
Ilya Dmitrievich Firsin
, 
Valeria Mikhailovna Trunina 1
Valeria Mikhailovna Trunina
, 
Vladislav Konstantinovich Gavrilov 1
Vladislav Konstantinovich Gavrilov
, 
Yan Pavlovich Bityak 4
Yan Pavlovich Bityak
, 
Denis A Fedorov 4
Denis A Fedorov
, 
Vladislav Sergeyevich Zimarev 1, 5
Vladislav Sergeyevich Zimarev
, 
Nataliya Sergeevna Goulioukina 1, 5, 6
Nataliya Sergeevna Goulioukina
1 Department of Chemistry, S.A. Esenin Ryazan State University, Ryazan, Russian Federation
2 I.P. Pavlov Ryazan State Medical University, Ryazan, Russian Federation
3 Scientific, Educational and Innovation Center for Chemical and Pharmaceutical Technologies, B.N. Yeltsin Ural Federal University, Ekaterinburg, Russian Federation
4 Moscow Institute of Physics and Technology (National Research University), Dolgoprudny, Moscow Region, Russian Federation
5 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
6 A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russian Federation
10.1016/j.mencom.2023.10.012
Published 2023-10-18
Communication , Volume 33, Issue 6, 776-778
3
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Gavrilov K. N. et al. TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 776-778.
GOST all authors (up to 50) Copy
Gavrilov K. N., Chuchelkin I. V., Shiryaev A. A., Firsin I. D., Trunina V. M., Gavrilov V. K., Bityak Y. P., Fedorov D. A., Zimarev V. S., Goulioukina N. S. TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 776-778.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.012
TI - TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions
T2 - Mendeleev Communications
AU - Gavrilov, Konstantin Nikolaevich
AU - Chuchelkin, Ilya Valer'evich
AU - Shiryaev, Alexei Aleksandrovich
AU - Firsin, Ilya Dmitrievich
AU - Trunina, Valeria Mikhailovna
AU - Gavrilov, Vladislav Konstantinovich
AU - Bityak, Yan Pavlovich
AU - Fedorov, Denis A
AU - Zimarev, Vladislav Sergeyevich
AU - Goulioukina, Nataliya Sergeevna
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 776-778
IS - 6
VL - 33
ER -
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@article{2023_Gavrilov,
author = {Konstantin Nikolaevich Gavrilov and Ilya Valer'evich Chuchelkin and Alexei Aleksandrovich Shiryaev and Ilya Dmitrievich Firsin and Valeria Mikhailovna Trunina and Vladislav Konstantinovich Gavrilov and Yan Pavlovich Bityak and Denis A Fedorov and Vladislav Sergeyevich Zimarev and Nataliya Sergeevna Goulioukina},
title = {TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.012},
number = {6},
pages = {776--778},
doi = {10.1016/j.mencom.2023.10.012}
}
MLA
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MLA Copy
Gavrilov, Konstantin Nikolaevich, et al. “TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 776-778. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.012.

Keywords

allylic substitution
asymmetric catalysis
hydrogenation
P
palladium
phosphoramidites
rhodium
S-ligands.

Abstract

Diastereomeric P,S-bidentate phosphoramidite ligands with TADDOL core and (1R,2S)-1,2-diphenyl-2-(phenylthio)-ethan-1-amine residue were synthesized. These ligands provided up to 76% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 70% ee in the amination of this substrate with pyrrolidine, and 89-95% ee in the Rh-catalyzed asymmetric hydro- genation of dimethyl itaconate and methyl (Z)-2-acetamido-3-arylacrylates. The different contributions of diastereomeric chiral inducers to the catalytic outcome are discussed.

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