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Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond

Liana Arthur Hayriyan 1
Liana Arthur Hayriyan
Anna F Mkrtchyan 1
Anna F Mkrtchyan
Margarita Alekseevna Moskalenko 2
Margarita Alekseevna Moskalenko
Zalina Taymurazovna Gugkaeva 2
Zalina Taymurazovna Gugkaeva
Mikhail Mikhailovich Ilyin 2
Mikhail Mikhailovich Ilyin
Kirill Konstantinovich Babievsky 2
Kirill Konstantinovich Babievsky
Pavel Vladimirovich Dorovatovskii
Victor Nikolaevich Khrustalev
Aleksandr Sergeevich Peregudov 2
Aleksandr Sergeevich Peregudov
Yurii Nikolaevich Belokon 2
Yurii Nikolaevich Belokon
Published 2018-09-07
CommunicationVolume 28, Issue 5, 464-466
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Hayriyan L. A. et al. Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 464-466.
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Hayriyan L. A., Mkrtchyan A. F., Moskalenko M. A., Maleev V. I., Gugkaeva Z. T., Ilyin M. M., Babievsky K. K., Dorovatovskii P. V., Khrustalev V. N., Peregudov A. S., Belokon Y. N. Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 464-466.
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TY - JOUR
DO - 10.1016/j.mencom.2018.09.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.003
TI - Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond
T2 - Mendeleev Communications
AU - Hayriyan, Liana Arthur
AU - Mkrtchyan, Anna F
AU - Moskalenko, Margarita Alekseevna
AU - Maleev, Victor Ivanovich
AU - Gugkaeva, Zalina Taymurazovna
AU - Ilyin, Mikhail Mikhailovich
AU - Babievsky, Kirill Konstantinovich
AU - Dorovatovskii, Pavel Vladimirovich
AU - Khrustalev, Victor Nikolaevich
AU - Peregudov, Aleksandr Sergeevich
AU - Belokon, Yurii Nikolaevich
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 464-466
IS - 5
VL - 28
ER -
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@article{2018_Hayriyan,
author = {Liana Arthur Hayriyan and Anna F Mkrtchyan and Margarita Alekseevna Moskalenko and Victor Ivanovich Maleev and Zalina Taymurazovna Gugkaeva and Mikhail Mikhailovich Ilyin and Kirill Konstantinovich Babievsky and Pavel Vladimirovich Dorovatovskii and Victor Nikolaevich Khrustalev and Aleksandr Sergeevich Peregudov and Yurii Nikolaevich Belokon},
title = {Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.003},
number = {5},
pages = {464--466},
doi = {10.1016/j.mencom.2018.09.003}
}
MLA
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Hayriyan, Liana Arthur, et al. “Nickel-coordinated chiral enols and Michael addition intermediate stabilized by the Ni–C bond.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 464-466. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.003.

Abstract

A representative within a new class of chiral enol NiII complexes derived from a Schiff base of aminoacetone and (S)-2-N-(N-benzylprolinoylamino)benzophenone was prepared, and its performance in nucleophilic addition was estimated. The complex was inert towards aldehydes and activated C=C bonds but reacted with carboxylic anhydrides and di-tert-butyl acetylenedicarboxylate. An unusual Michael addition intermediate stabilized by the Ni–C bond was discovered in the latter reaction.

References

1.
10.1016/j.mencom.2018.09.003_sbref0005a
Rouhi
C&EN, 2003
2.
Academia–Industry Symbiosis in Organic Chemistry
Michaudel Q., Ishihara Y., Baran P.S.
Accounts of Chemical Research, 2015
3.
The Growing Impact of Catalysis in the Pharmaceutical Industry
Busacca C.A., Fandrick D.R., Song J.J., Senanayake C.H.
Advanced Synthesis and Catalysis, 2011
4.
10.1016/j.mencom.2018.09.003_sbref0005d
Waser
Asymmetric Organocatalysis in Natural Product Syntheses, 2012
7.
Methods for (11) C- and (18) F-labelling of amino acids and derivatives for positron emission tomography imaging.
Ermert J., Coenen H.H.
Journal of Labelled Compounds and Radiopharmaceuticals, 2013
8.
10.1016/j.mencom.2018.09.003_sbref0010c
Hanson
The Organic Chemistry of Isotopic Labelling, 2011
10.
General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine
Belokon Y.N., Bulychev A.G., Vitt S.V., Struchkov Y.T., Batsanov A.S., Timofeeva T.V., Tsyryapkin V.A., Ryzhov M.G., Lysova L.A.
Journal of the American Chemical Society, 1985
11.
General method for the asymmetric synthesis of α-amino acids via alkylation of the chiral nickel(II) Schiff base complexes of glycine and alanine
Belokon Y.N., Bakhmutov V.I., Chernoglazova N.I., Kochetkov K.A., Vitt S.V., Garbalinskaya N.S., Belikov V.M.
Journal of the Chemical Society Perkin Transactions 1, 1988
12.
Belokon Y.N., Kochetkov K.A., Borkin D.A.
Mendeleev Communications, 2003
13.
Synthesis of enantio- and diastereoiso-merically pure substituted prolines via condensation of glycine with olefins activated by a carbonyl group
Beloko? Y.N., Bulychev A.G., Pavlov V.A., Fedorova E.B., Tsyryapkin V.A., Bakhmutov V.A., Belikov V.M.
Journal of the Chemical Society Perkin Transactions 1, 1988
14.
Asymmetric synthesis of β-substituted α-amino acids via a chiral nlii complex of dehydroalanine
Belokon' Y.N., Sagyan A.S., Djamgaryan S.M., Bakhmutov V.I., Belikov V.M.
Tetrahedron, 1988
15.
Synthesis of a chiral nickel(II) complex of an electrophilic glycinate, and its use for asymmetric preparation of α-amino acids
Belokoń Y.N., Popkov A.N., Chernoglazova N.I., Saporovskaya M.B., Bakhmutov V.I., Belikov V.M.
Journal of the Chemical Society Chemical Communications, 1988
17.
Improved Synthesis of the Unnatural Amino Acids AHMOD and AMD, Components of the Anticancer Peptaibol Culicinin D
Ko K., Wagner S., Yang S., Furkert D.P., Brimble M.A.
Journal of Organic Chemistry, 2015
21.
Asymmetric Carbon-Carbon Bond Formation under Solventless Conditions in Ball Mills
Jörres M., Aceña J.L., Soloshonok V.A., Bolm C.
ChemCatChem, 2015
22.
Nα-Fmoc-Protected ω-Azido- and ω-Alkynyl-L-amino Acids as Building Blocks for the Synthesis of “Clickable” Peptides
Le Chevalier Isaad A., Barbetti F., Rovero P., D'Ursi A.M., Chelli M., Chorev M., Papini A.M.
European Journal of Organic Chemistry, 2008
24.
10.1016/j.mencom.2018.09.003_sbref0020h
Saghyan
J. Chem. Eng. Appl., 2016
27.
Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes
Wang Y., Song X., Wang J., Moriwaki H., Soloshonok V.A., Liu H.
Amino Acids, 2017