Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation
I V Chuchelkin
1
,
I D Firsin
1
,
Vladislav S Zimarev
1, 3
,
Andrey A Denesh
2
,
N S Goulioukina
1, 3, 4
1
2
3
Publication type: Journal Article
Publication date: 2021-09-01
scimago Q3
wos Q3
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
Abstract
The reaction of P ,S-phosphoramidite bearing ( R a )-BIPHEN H2 core and exocyclic amino sulfide as the new ligand with [Pd(ppp-allyl)Cl] 2 in the presence of AgBF 4 yielded a cationic metallochelate [Pd(ppp-allyl)(L)]BF 4 . This new chiral inducer provided up to 90% ee in the Pd-mediated allylic substitution reaction of ( E )-1,3-diphenylallyl acetate with various C- and N-nucleophiles. In the Pd-catalyzed amination of 2-diethoxyphosphoryl-1-phenylallyl acetate with aniline, ee values up to 57% were achieved.
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Total citations:
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Gavrilov K. N. et al. Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 651-653.
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Gavrilov K. N., Chuchelkin I. V., Zheglov S. V., Firsin I. D., Trunina V. M., Gavrilov V. K., Borisova N. E., Zimarev V. S., Denesh A. A., Goulioukina N. S. Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 651-653.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.019
UR - https://doi.org/10.1016/j.mencom.2021.09.019
TI - Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation
T2 - Mendeleev Communications
AU - Gavrilov, Konstantin N.
AU - Chuchelkin, I V
AU - Zheglov, Sergey V.
AU - Firsin, I D
AU - Trunina, Valeria M
AU - Gavrilov, Vladislav K
AU - Borisova, Nataliya E.
AU - Zimarev, Vladislav S
AU - Denesh, Andrey A
AU - Goulioukina, N S
PY - 2021
DA - 2021/09/01
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 651-653
IS - 5
VL - 31
SN - 0959-9436
SN - 1364-551X
ER -
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@article{2021_Gavrilov,
author = {Konstantin N. Gavrilov and I V Chuchelkin and Sergey V. Zheglov and I D Firsin and Valeria M Trunina and Vladislav K Gavrilov and Nataliya E. Borisova and Vladislav S Zimarev and Andrey A Denesh and N S Goulioukina},
title = {Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {sep},
url = {https://doi.org/10.1016/j.mencom.2021.09.019},
number = {5},
pages = {651--653},
doi = {10.1016/j.mencom.2021.09.019}
}
Cite this
MLA
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Gavrilov, Konstantin N., et al. “Novel BIPHEN H2 based P,S-bidentate phosphoramidite ligand in palladium-catalyzed asymmetric allylation.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 651-653. https://doi.org/10.1016/j.mencom.2021.09.019.