TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions
I V Chuchelkin
1
,
Alexey A Shiryaev
2, 3
,
I D Firsin
1
,
Vladislav K Gavrilov
1
,
Yan P. Bityak
4
,
Denis A Fedorov
4
,
Vladislav S Zimarev
1, 5
,
N S Goulioukina
1, 5, 6
1
4
5
Publication type: Journal Article
Publication date: 2023-11-29
scimago Q3
wos Q3
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
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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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.
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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://doi.org/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 N.
AU - Chuchelkin, I V
AU - Shiryaev, Alexey A
AU - Firsin, I D
AU - Trunina, Valeria M
AU - Gavrilov, Vladislav K
AU - Bityak, Yan P.
AU - Fedorov, Denis A
AU - Zimarev, Vladislav S
AU - Goulioukina, N S
PY - 2023
DA - 2023/11/29
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 776-778
IS - 6
VL - 33
SN - 0959-9436
SN - 1364-551X
ER -
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BibTex (up to 50 authors)
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@article{2023_Gavrilov,
author = {Konstantin N. Gavrilov and I V Chuchelkin and Alexey A Shiryaev and I D Firsin and Valeria M Trunina and Vladislav K Gavrilov and Yan P. Bityak and Denis A Fedorov and Vladislav S Zimarev and N S Goulioukina},
title = {TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {nov},
url = {https://doi.org/10.1016/j.mencom.2023.10.012},
number = {6},
pages = {776--778},
doi = {10.1016/j.mencom.2023.10.012}
}
Cite this
MLA
Copy
Gavrilov, Konstantin N., et al. “TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions.” Mendeleev Communications, vol. 33, no. 6, Nov. 2023, pp. 776-778. https://doi.org/10.1016/j.mencom.2023.10.012.