Home / Publications / Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis

Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis

Mikhail Alekseevich Emelyanov 1
Mikhail Alekseevich Emelyanov
, 
Evgeniy Vadimovich Rozhkov 1, 2
Evgeniy Vadimovich Rozhkov
,  , 
Vladimir Anatol'evich Larionov 1
Vladimir Anatol'evich Larionov
1 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
2 Higher Chemical College of the Russian Academy of Sciences, D.I. Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
10.1016/j.mencom.2024.02.015
Published 2024-02-19
Communication , Volume 34, Issue 2, 206-208
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Emelyanov M. A. et al. Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 206-208.
GOST all authors (up to 50) Copy
Emelyanov M. A., Rozhkov E. V., Maleev V. I., Larionov V. A. Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 206-208.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.02.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.015
TI - Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis
T2 - Mendeleev Communications
AU - Emelyanov, Mikhail Alekseevich
AU - Rozhkov, Evgeniy Vadimovich
AU - Maleev, Victor Ivanovich
AU - Larionov, Vladimir Anatol'evich
PY - 2024
DA - 2024/02/19
PB - Mendeleev Communications
SP - 206-208
IS - 2
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Emelyanov,
author = {Mikhail Alekseevich Emelyanov and Evgeniy Vadimovich Rozhkov and Victor Ivanovich Maleev and Vladimir Anatol'evich Larionov},
title = {Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.015},
number = {2},
pages = {206--208},
doi = {10.1016/j.mencom.2024.02.015}
}
MLA
Cite this
MLA Copy
Emelyanov, Mikhail Alekseevich, et al. “Dynamic kinetic resolution of an azlactone catalyzed by octahedral chiral-at-metal cobalt(III) complexes under phase-transfer alcoholysis.” Mendeleev Communications, vol. 34, no. 2, Feb. 2024, pp. 206-208. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.015.

Keywords

amino acids
azlactone
chiral-at-metal
cobalt(III) complexes.
kinetic resolution

Abstract

A family of well-defined octahedral cationic chiral-at- cobalt(III) catalysts based on (R,R)-1,2-cyclohexanediamine and (R,R)-1,2-diphenylethylenediamine has been examined in the dynamic kinetic resolution of an azlactone derived from N-benzoyl-tert-leucine. The reactions catalyzed by 10 mol% of CoIII complexes in the presence of 1 M aqueous NaOH solution under phase-transfer alcoholysis afforded the corresponding benzyl ester of tert-leucine with up to 76% yield and up to 66% enantioselectivity (ee).

References

.
Recent developments in asymmetric phase-transfer reactions.
Shirakawa S., Maruoka K.
Angewandte Chemie - International Edition, 2013
.
Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone
Belokon Y., Gugkaeva Z., Larionov V., Moskalenko M., Khrustalev V., Nelyubina Y., Peregudov A., Tsaloev A., Maleev V.
Synthesis, 2017
.
Chiral Octahedral Complexes of CoIII As a Family of Asymmetric Catalysts Operating under Phase Transfer Conditions
Belokon Y.N., Maleev V.I., North M., Larionov V.A., Savel’yeva T.F., Nijland A., Nelyubina Y.V.
ACS Catalysis, 2013
.
Unusual Amino Acids in Medicinal Chemistry
Blaskovich M.A.
Journal of Medicinal Chemistry, 2016
.
Rational Design of 2-Substituted DMAP-N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones
Xie M., Huang B., Li N., Tian Y., Wu X., Deng Y., Qu G., Guo H.
Journal of the American Chemical Society, 2020
.
Amino Acid Schiff Base Bearing Benzophenone Imine As a Platform for Highly Congested Unnatural α-Amino Acid Synthesis
Matsumoto Y., Sawamura J., Murata Y., Nishikata T., Yazaki R., Ohshima T.
Journal of the American Chemical Society, 2020
.
Dynamic Kinetic Resolution of Azlactones via Phase-Transfer Catalytic Alcoholysis
Wakafuji K., Iwasa S., Ouchida K.N., Cho H., Dohi H., Yamamoto E., Kamachi T., Tokunaga M.
ACS Catalysis, 2021
.
Advances in Asymmetric Amino Acid Synthesis Enabled by Radical Chemistry
Larionov V.A., Stoletova N.V., Maleev V.I.
Advanced Synthesis and Catalysis, 2020
.
Enzymatic asymmetric synthesis of chiral amino acids
Xue Y., Cao C., Zheng Y.
Chemical Society Reviews, 2018
.
Future prospects for noncanonical amino acids in biological therapeutics
Rezhdo A., Islam M., Huang M., Van Deventer J.A.
Current Opinion in Biotechnology, 2019