Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols
Konstantin N. Gavrilov
1, 2, 3
,
Sergey V. Zheglov
1, 2, 3
,
Vladislav K Gavrilov
1, 2, 3
,
Marina G Maksimova
1, 2, 3
,
В. А. Тафеенко
4
,
V. V. Chernyshev
4
,
Kirill P. Birin
5
,
1
DEPARTMENT OF CHEMISTRY
3
46 Svoboda Street 390000 Ryazan Russian Federation
|
Publication type: Journal Article
Publication date: 2017-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A small series of P*,P*-bidentate bisdiamidophosphite ligands containing 1,3,2-diazaphospholidine rings have been prepared. The cationic [Pd(allyl)(P*,P*)]BF4 and neutral [Pd(P*,P*)Cl2] palladium(II) complexes were synthesized with one of the new ligands. The use of these ligands provides up to 98% ee in Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate, up to 72% ee in Pd-catalyzed asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate and up to 94% ee in Pd-catalyzed desymmetrization of N,N'-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate. The influence of the nature of the bridging ligand fragments of the bisdiamidophosphites on asymmetric induction is discussed.
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Gavrilov K. N. et al. Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols // Tetrahedron. 2017. Vol. 73. No. 5. pp. 461-471.
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Gavrilov K. N., Zheglov S. V., Gavrilov V. K., Maksimova M. G., Тафеенко В. А., Chernyshev V. V., Birin K. P., Mikhel I. S. Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols // Tetrahedron. 2017. Vol. 73. No. 5. pp. 461-471.
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RIS
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TY - JOUR
DO - 10.1016/j.tet.2016.12.023
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402016313011
TI - Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols
T2 - Tetrahedron
AU - Gavrilov, Konstantin N.
AU - Zheglov, Sergey V.
AU - Gavrilov, Vladislav K
AU - Maksimova, Marina G
AU - Тафеенко, В. А.
AU - Chernyshev, V. V.
AU - Birin, Kirill P.
AU - Mikhel, Igor S
PY - 2017
DA - 2017/02/01
PB - Elsevier
SP - 461-471
IS - 5
VL - 73
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2017_Gavrilov,
author = {Konstantin N. Gavrilov and Sergey V. Zheglov and Vladislav K Gavrilov and Marina G Maksimova and В. А. Тафеенко and V. V. Chernyshev and Kirill P. Birin and Igor S Mikhel},
title = {Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols},
journal = {Tetrahedron},
year = {2017},
volume = {73},
publisher = {Elsevier},
month = {feb},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040402016313011},
number = {5},
pages = {461--471},
doi = {10.1016/j.tet.2016.12.023}
}
Cite this
MLA
Copy
Gavrilov, Konstantin N., et al. “Palladium catalyzed asymmetric reactions assisted by P*,P*-bidentate bisdiamidophosphites based on 1,4-diols.” Tetrahedron, vol. 73, no. 5, Feb. 2017, pp. 461-471. https://linkinghub.elsevier.com/retrieve/pii/S0040402016313011.