Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones
A number of new chiral bispidines containing monoterpenoid fragments have been obtained. 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 s...
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MDPI AG
2021-12-01
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| author | Evgeniy V. Suslov Konstantin Y. Ponomarev Oxana S. Patrusheva Sergey O. Kuranov Alina A. Okhina Artem D. Rogachev Aldar A. Munkuev Roman V. Ottenbacher Alexander I. Dalinger Mikhail A. Kalinin Sergey Z. Vatsadze Konstantin P. Volcho Nariman F. Salakhutdinov |
| author_facet | Evgeniy V. Suslov Konstantin Y. Ponomarev Oxana S. Patrusheva Sergey O. Kuranov Alina A. Okhina Artem D. Rogachev Aldar A. Munkuev Roman V. Ottenbacher Alexander I. Dalinger Mikhail A. Kalinin Sergey Z. Vatsadze Konstantin P. Volcho Nariman F. Salakhutdinov |
| author_sort | Evgeniy V. Suslov |
| collection | DOAJ |
| description | A number of new chiral bispidines containing monoterpenoid fragments have been obtained. 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. |
| first_indexed | 2024-03-10T03:29:01Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:29:01Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-24d498af424d4ac98892b5e3ea3dd2d12023-11-23T09:45:38ZengMDPI AGMolecules1420-30492021-12-012624753910.3390/molecules26247539Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of ChalconesEvgeniy V. Suslov0Konstantin Y. Ponomarev1Oxana S. Patrusheva2Sergey O. Kuranov3Alina A. Okhina4Artem D. Rogachev5Aldar A. Munkuev6Roman V. Ottenbacher7Alexander I. Dalinger8Mikhail A. Kalinin9Sergey Z. Vatsadze10Konstantin P. Volcho11Nariman F. Salakhutdinov12Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaBoreskov Institute of Catalysis SB RAS, Lavrent’ev Av., 5, 630090 Novosibirsk, RussiaChemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, 119991 Moscow, RussiaChemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, 119991 Moscow, RussiaChemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, 119991 Moscow, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, RussiaA number of new chiral bispidines containing monoterpenoid fragments have been obtained. 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.https://www.mdpi.com/1420-3049/26/24/7539bispidinesmonoterpenoidscatalysisdialkylzincs additionchalconesnatural compounds |
| spellingShingle | Evgeniy V. Suslov Konstantin Y. Ponomarev Oxana S. Patrusheva Sergey O. Kuranov Alina A. Okhina Artem D. Rogachev Aldar A. Munkuev Roman V. Ottenbacher Alexander I. Dalinger Mikhail A. Kalinin Sergey Z. Vatsadze Konstantin P. Volcho Nariman F. Salakhutdinov Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones Molecules bispidines monoterpenoids catalysis dialkylzincs addition chalcones natural compounds |
| title | Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones |
| title_full | Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones |
| title_fullStr | Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones |
| title_full_unstemmed | Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones |
| title_short | Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones |
| title_sort | novel bispidine monoterpene conjugates synthesis and application as ligands for the catalytic ethylation of chalcones |
| topic | bispidines monoterpenoids catalysis dialkylzincs addition chalcones natural compounds |
| url | https://www.mdpi.com/1420-3049/26/24/7539 |
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