Home / Publications / Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines

Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines

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10.1016/j.mencom.2016.11.005
Published 2016-10-27
Communication , Volume 26, Issue 6, 477-479
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Tarasenko E. A., Beletskaya I. P. Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines // Mendeleev Communications. 2016. Vol. 26. No. 6. pp. 477-479.
GOST all authors (up to 50) Copy
Tarasenko E. A., Beletskaya I. P. Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines // Mendeleev Communications. 2016. Vol. 26. No. 6. pp. 477-479.
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TY - JOUR
DO - 10.1016/j.mencom.2016.11.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.005
TI - Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines
T2 - Mendeleev Communications
AU - Tarasenko, Elena Aleksandrovna
AU - Beletskaya, Irina Petrovna
PY - 2016
DA - 2016/10/27
PB - Mendeleev Communications
SP - 477-479
IS - 6
VL - 26
ER -
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@article{2016_Tarasenko,
author = {Elena Aleksandrovna Tarasenko and Irina Petrovna Beletskaya},
title = {Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines},
journal = {Mendeleev Communications},
year = {2016},
volume = {26},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.005},
number = {6},
pages = {477--479},
doi = {10.1016/j.mencom.2016.11.005}
}
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Tarasenko, Elena Aleksandrovna, and Irina Petrovna Beletskaya. “Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in Cui-catalyzed enantioselective direct addition of terminal alkynes to imines.” Mendeleev Communications, vol. 26, no. 6, Oct. 2016, pp. 477-479. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.11.005.

Abstract

Pyridine-2,6-bis(oxazoline) immobilized on a soluble support, viz., poly(ethylene glycol) methyl ether with Mn = 5000 Da, has been synthesized for the first time. The efficiency of its application as a chiral ligand in Cui-catalyzed direct addition of terminal alkynes to imines and the feasibility of its recycling at least in three cycles have been shown.

References

1.
Pyridine-2,6-bis(oxazolines), Helpful Ligands for Asymmetric Catalysts
Desimoni G., Faita G., Quadrelli P.
Chemical Reviews, 2003
3.
Rare earth metal oxazoline complexes in asymmetric catalysis
Ward B.D., Gade L.H.
Chemical Communications, 2012
5.
The First Immobilization of Pyridine-bis(oxazoline) Chiral Ligands
Cornejo A., Fraile J.M., García J.I., García-Verdugo E., Gil M.J., Legarreta G., Luis S.V., Martínez-Merino V., Mayoral J.A.
Organic Letters, 2002
7.
The First Solid-Phase Synthesis of Bis(oxazolinyl)pyridine Ligands
Weissberg A., Halak B., Portnoy M.
Journal of Organic Chemistry, 2005
8.
A Flexible and Versatile Strategy for the Covalent Immobilization of Chiral Catalysts Based on Pyridinebis(oxazoline) Ligands
Cornejo A., Fraile J.M., García J.I., Gil M.J., Luis S.V., Martínez-Merino V., Mayoral J.A.
Journal of Organic Chemistry, 2005
9.
Polymer-Bound Pyridine-Bis(oxazoline). Preparation through Click Chemistry and Evaluation in Asymmetric Catalysis
Tilliet M., Lundgren S., Moberg C., Levacher V.
Advanced Synthesis and Catalysis, 2007
15.
Cu(II)−Aza(bisoxazoline)-Catalyzed Asymmetric Benzoylations
Gissibl A., Finn M.G., Reiser O.
Organic Letters, 2005
16.
Poly(ethylene glycol)-Supported Bisoxazolines as Ligands for Catalytic Enantioselective Synthesis
Annunziata R., Benaglia M., Cinquini M., Cozzi F., Pitillo M.
Journal of Organic Chemistry, 2001
19.
10.1016/j.mencom.2016.11.005_bib0095
Click Chemistry for Biotechnology and Materials Science, 2009
20.
Cu-Catalyzed Azide−Alkyne Cycloaddition
Meldal M., Tornøe C.W.
Chemical Reviews, 2008
21.
Click Chemistry for Drug Development and Diverse Chemical–Biology Applications
Thirumurugan P., Matosiuk D., Jozwiak K.
Chemical Reviews, 2013
24.
Recent Developments in Asymmetric Alkynylation of Imines
Blay G., Monleon A., Pedro J.
Current Organic Chemistry, 2009
25.
The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups
Trost B., Weiss A.
Advanced Synthesis and Catalysis, 2009
26.
10.1016/j.mencom.2016.11.005_bib0130
Yoo
Aldrichimica Acta, 2011
28.
Asymmetric Catalysis Special Feature Part II: Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines
Wei C., Mague J.T., Li C.
Proceedings of the National Academy of Sciences of the United States of America, 2004