Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions
3
RUSSIAN ACADEMY OF SCIENCES
4
Leninskiy prospekt 31/4 119071 Moscow Russian Federation
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Publication type: Journal Article
Publication date: 2016-12-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Abstract We have designed and synthesized a small library of readily available P,N,N-diamidophosphite–oxazoline ligands containing 1,3,2-diazaphospholidine rings and a pyridine moiety. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate; up to 80% ee in the Pd-catalyzed asymmetric alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate and up to 94% ee in the Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate. The influence of the structural modules, such as the nature of the phosphorus containing ring or pyridine substituent as well as of the addition of zinc(II) 5,10,15,20-tetraphenylporphyrin on the catalytic activity and enantioselectivity is discussed.
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Gavrilov K. N. et al. Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions // Tetrahedron Asymmetry. 2016. Vol. 27. No. 24. pp. 1260-1268.
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Gavrilov K. N., Zheglov S. V., Novikov I. M., Lugovsky V. V., Zimarev V. S., Mikhel I. S. Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions // Tetrahedron Asymmetry. 2016. Vol. 27. No. 24. pp. 1260-1268.
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TY - JOUR
DO - 10.1016/j.tetasy.2016.10.008
UR - https://linkinghub.elsevier.com/retrieve/pii/S0957416616303019
TI - Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions
T2 - Tetrahedron Asymmetry
AU - Gavrilov, Konstantin N.
AU - Zheglov, Sergey V.
AU - Novikov, Ivan M
AU - Lugovsky, Victor V
AU - Zimarev, Vladislav S
AU - Mikhel, Igor S
PY - 2016
DA - 2016/12/01
PB - Elsevier
SP - 1260-1268
IS - 24
VL - 27
SN - 0957-4166
SN - 1362-511X
ER -
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@article{2016_Gavrilov,
author = {Konstantin N. Gavrilov and Sergey V. Zheglov and Ivan M Novikov and Victor V Lugovsky and Vladislav S Zimarev and Igor S Mikhel},
title = {Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions},
journal = {Tetrahedron Asymmetry},
year = {2016},
volume = {27},
publisher = {Elsevier},
month = {dec},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0957416616303019},
number = {24},
pages = {1260--1268},
doi = {10.1016/j.tetasy.2016.10.008}
}
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MLA
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Gavrilov, Konstantin N., et al. “Diamidophosphite–oxazolines with a pyridine core in Pd-catalyzed asymmetric reactions.” Tetrahedron Asymmetry, vol. 27, no. 24, Dec. 2016, pp. 1260-1268. https://linkinghub.elsevier.com/retrieve/pii/S0957416616303019.