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Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones. / Suslov, Evgeniy V.; Ponomarev, Konstantin Y.; Patrusheva, Oxana S. et al.

In: Molecules, Vol. 26, No. 24, 7539, 01.12.2021.

Research output: Contribution to journal › Article › peer-review

Harvard

Suslov, EV, Ponomarev, KY, Patrusheva, OS, Kuranov, SO, Okhina, AA, Rogachev, AD, Munkuev, AA, Ottenbacher, RV, Dalinger, AI, Kalinin, MA, Vatsadze, SZ, Volcho, KP & Salakhutdinov, NF 2021, 'Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones', Molecules, vol. 26, no. 24, 7539. https://doi.org/10.3390/molecules26247539

APA

Suslov, E. V., Ponomarev, K. Y., Patrusheva, O. S., Kuranov, S. O., Okhina, A. A., Rogachev, A. D., Munkuev, A. A., Ottenbacher, R. V., Dalinger, A. I., Kalinin, M. A., Vatsadze, S. Z., Volcho, K. P., & Salakhutdinov, N. F. (2021). Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones. Molecules, 26(24), [7539]. https://doi.org/10.3390/molecules26247539

Vancouver

Suslov EV, Ponomarev KY, Patrusheva OS, Kuranov SO, Okhina AA, Rogachev AD et al. Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones. Molecules. 2021 Dec 1;26(24):7539. doi: 10.3390/molecules26247539

Author

Suslov, Evgeniy V. ; Ponomarev, Konstantin Y. ; Patrusheva, Oxana S. et al. / Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones. In: Molecules. 2021 ; Vol. 26, No. 24.

BibTeX

@article{6fdd66cdf0a04da78fc8bf3c7052bb42,
title = "Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones",
abstract = "A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed, in which the peaks of the enantiomers of all synthesized chiral products were separated, which made it possible to determine the enantiomeric excess of the resulting mixture. It was demonstrated that bispidine-monoterpenoid conjugates can be used as the ligands for diethylzinc addition to chalcone C=C double bond but not as inducers of chirality. Besides products of ethylation, formation of products of formal hydrogenation of the chalcone C=C double bond was observed in all cases. Note, that this formation of hydrogenation products in significant amounts in the presence of such catalytic systems was found for the first time. A tentative scheme explaining the formation of all products was proposed.",
keywords = "Bispidines, Catalysis, Chalcones, Chiral ligands, Dialkylzincs addition, Ethylation, Monoterpenoids, Natural compounds, Nickel complexes",
author = "Suslov, {Evgeniy V.} and Ponomarev, {Konstantin Y.} and Patrusheva, {Oxana S.} and Kuranov, {Sergey O.} and Okhina, {Alina A.} and Rogachev, {Artem D.} and Munkuev, {Aldar A.} and Ottenbacher, {Roman V.} and Dalinger, {Alexander I.} and Kalinin, {Mikhail A.} and Vatsadze, {Sergey Z.} and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.}",
note = "Funding Information: Funding: This work was financially supported by the Russian Science Foundation (grant 19-73-20090). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",
year = "2021",
month = dec,
day = "1",
doi = "10.3390/molecules26247539",
language = "English",
volume = "26",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones

AU - Suslov, Evgeniy V.

AU - Ponomarev, Konstantin Y.

AU - Patrusheva, Oxana S.

AU - Kuranov, Sergey O.

AU - Okhina, Alina A.

AU - Rogachev, Artem D.

AU - Munkuev, Aldar A.

AU - Ottenbacher, Roman V.

AU - Dalinger, Alexander I.

AU - Kalinin, Mikhail A.

AU - Vatsadze, Sergey Z.

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

N1 - Funding Information: Funding: This work was financially supported by the Russian Science Foundation (grant 19-73-20090). Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/12/1

Y1 - 2021/12/1

N2 - A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed, in which the peaks of the enantiomers of all synthesized chiral products were separated, which made it possible to determine the enantiomeric excess of the resulting mixture. It was demonstrated that bispidine-monoterpenoid conjugates can be used as the ligands for diethylzinc addition to chalcone C=C double bond but not as inducers of chirality. Besides products of ethylation, formation of products of formal hydrogenation of the chalcone C=C double bond was observed in all cases. Note, that this formation of hydrogenation products in significant amounts in the presence of such catalytic systems was found for the first time. A tentative scheme explaining the formation of all products was proposed.

AB - A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed, in which the peaks of the enantiomers of all synthesized chiral products were separated, which made it possible to determine the enantiomeric excess of the resulting mixture. It was demonstrated that bispidine-monoterpenoid conjugates can be used as the ligands for diethylzinc addition to chalcone C=C double bond but not as inducers of chirality. Besides products of ethylation, formation of products of formal hydrogenation of the chalcone C=C double bond was observed in all cases. Note, that this formation of hydrogenation products in significant amounts in the presence of such catalytic systems was found for the first time. A tentative scheme explaining the formation of all products was proposed.

KW - Bispidines

KW - Catalysis

KW - Chalcones

KW - Chiral ligands

KW - Dialkylzincs addition

KW - Ethylation

KW - Monoterpenoids

KW - Natural compounds

KW - Nickel complexes

UR - http://www.scopus.com/inward/record.url?scp=85121206812&partnerID=8YFLogxK

U2 - 10.3390/molecules26247539

DO - 10.3390/molecules26247539

M3 - Article

C2 - 34946622

AN - SCOPUS:85121206812

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 7539

ER -

ID: 35033351