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First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions

Konstantin Nikolaevich Gavrilov 1
Konstantin Nikolaevich Gavrilov
, 
Ilya Valer'evich Chuchelkin 1
Ilya Valer'evich Chuchelkin
, 
Sergey Viktorovich Zheglov 1
Sergey Viktorovich Zheglov
, 
Ilya Dmitrievich Firsin 1
Ilya Dmitrievich Firsin
,  , 
Vladislav Konstantinovich Gavrilov 1
Vladislav Konstantinovich Gavrilov
, 
Alexander Vital'evich Maximychev 2
Alexander Vital'evich Maximychev
, 
Alexander Maksimovich Perepukhov 2
Alexander Maksimovich Perepukhov
, 
Nataliya Sergeevna Goulioukina 1, 3, 4
Nataliya Sergeevna Goulioukina
10.1016/j.mencom.2020.01.010
Published 2019-12-30
Communication , Volume 30, Issue 1, 31-33
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Gavrilov K. N. et al. First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 31-33.
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Gavrilov K. N., Chuchelkin I. V., Zheglov S. V., Firsin I. D., Zimarev V. S., Gavrilov V. K., Maximychev A. V., Perepukhov A. M., Goulioukina N. S. First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 31-33.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.010
TI - First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions
T2 - Mendeleev Communications
AU - Gavrilov, Konstantin Nikolaevich
AU - Chuchelkin, Ilya Valer'evich
AU - Zheglov, Sergey Viktorovich
AU - Firsin, Ilya Dmitrievich
AU - Zimarev, Vladislav Sergeyevich
AU - Gavrilov, Vladislav Konstantinovich
AU - Maximychev, Alexander Vital'evich
AU - Perepukhov, Alexander Maksimovich
AU - Goulioukina, Nataliya Sergeevna
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 31-33
IS - 1
VL - 30
ER -
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@article{2019_Gavrilov,
author = {Konstantin Nikolaevich Gavrilov and Ilya Valer'evich Chuchelkin and Sergey Viktorovich Zheglov and Ilya Dmitrievich Firsin and Vladislav Sergeyevich Zimarev and Vladislav Konstantinovich Gavrilov and Alexander Vital'evich Maximychev and Alexander Maksimovich Perepukhov and Nataliya Sergeevna Goulioukina},
title = {First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.010},
number = {1},
pages = {31--33},
doi = {10.1016/j.mencom.2020.01.010}
}
MLA
Cite this
MLA Copy
Gavrilov, Konstantin Nikolaevich, et al. “First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 31-33. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.010.

Keywords

chiral diamidophosphites
chiral P,S-ligands
palladium-catalyzed asymmetric reactions

Abstract

A novel P*,S-bidentate diamidophosphite ligand with a 1,3,2-diazaphospholidine core and an exocyclic thioether fragment provided up to 86% ee in the Pd-catalyzed alkylation of rac-(E)-1,3-diphenylallyl acetate with dimethyl malonate, as well as up to 73 and 75% ee in the amination of this substrate with pyrrolidine and diethyl (aminomethyl)phosphonate, respectively. For the Pd-catalyzed alkylation of cinnamyl acetate with β-keto esters, ee values up to 76% were achieved.

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