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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Published inMolecules (Basel, Switzerland) Vol. 26; no. 24; p. 7539
Main Authors Suslov, Evgeniy V., Ponomarev, Konstantin Y., Patrusheva, Oxana S., Kuranov, Sergey O., Okhina, Alina A., Rogachev, Artem D., Munkuev, Aldar A., Ottenbacher, Roman V., Dalinger, Alexander I., Kalinin, Mikhail A., Vatsadze, Sergey Z., Volcho, Konstantin P., Salakhutdinov, Nariman F.
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 13.12.2021
MDPI
Subjects
Alcohol
bispidines
catalysis
chalcones
Chloride
dialkylzincs addition
Hydrochloric acid
Iodine
Ligands
monoterpenoids
natural compounds
Nitrogen
chalcones
natural compounds
dialkylzincs addition
catalysis
ethylation
monoterpenoids
chiral ligands
bispidines
nickel complexes
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Abstract 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.
AbstractList 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.
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.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.
Author Ottenbacher, Roman V.
Dalinger, Alexander I.
Rogachev, Artem D.
Vatsadze, Sergey Z.
Salakhutdinov, Nariman F.
Ponomarev, Konstantin Y.
Okhina, Alina A.
Patrusheva, Oxana S.
Kalinin, Mikhail A.
Suslov, Evgeniy V.
Munkuev, Aldar A.
Volcho, Konstantin P.
Kuranov, Sergey O.
AuthorAffiliation 1 Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, Russia; suslov@nioch.nsc.ru (E.V.S.); ponomarev@nioch.nsc.ru (K.Y.P.); bawos@nioch.nsc.ru (O.S.P.); skuranov@nioch.nsc.ru (S.O.K.); aokhina@nioch.nsc.ru (A.A.O.); rogachev@nioch.nsc.ru (A.D.R.); amunkuev@nioch.nsc.ru (A.A.M.); anvar@nioch.nsc.ru (N.F.S.)
3 Boreskov Institute of Catalysis SB RAS, Lavrent’ev Av., 5, 630090 Novosibirsk, Russia; ottenbacher@catalysis.ru
2 Faculty of Natural Sciences, Novosibirsk State University, Pirogov Str., 2, 630090 Novosibirsk, Russia
4 Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, 119991 Moscow, Russia; dal1995@mail.ru (A.I.D.); chem.kalinin@gmail.com (M.A.K.)
AuthorAffiliation_xml – name: 1 Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, 630090 Novosibirsk, Russia; suslov@nioch.nsc.ru (E.V.S.); ponomarev@nioch.nsc.ru (K.Y.P.); bawos@nioch.nsc.ru (O.S.P.); skuranov@nioch.nsc.ru (S.O.K.); aokhina@nioch.nsc.ru (A.A.O.); rogachev@nioch.nsc.ru (A.D.R.); amunkuev@nioch.nsc.ru (A.A.M.); anvar@nioch.nsc.ru (N.F.S.)
– name: 3 Boreskov Institute of Catalysis SB RAS, Lavrent’ev Av., 5, 630090 Novosibirsk, Russia; ottenbacher@catalysis.ru
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– name: 2 Faculty of Natural Sciences, Novosibirsk State University, Pirogov Str., 2, 630090 Novosibirsk, Russia
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/34946622$$D View this record in MEDLINE/PubMed
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Issue 24
Keywords chalcones
natural compounds
dialkylzincs addition
catalysis
ethylation
monoterpenoids
chiral ligands
bispidines
nickel complexes
Language English
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Snippet A number of new chiral bispidines containing monoterpenoid fragments have been obtained. The bispidines were studied as ligands for Ni-catalyzed addition of...
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StartPage 7539
SubjectTerms Alcohol
bispidines
catalysis
chalcones
Chloride
dialkylzincs addition
Hydrochloric acid
Iodine
Ligands
monoterpenoids
natural compounds
Nitrogen
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Title Novel Bispidine-Monoterpene Conjugates—Synthesis and Application as Ligands for the Catalytic Ethylation of Chalcones
URI https://www.ncbi.nlm.nih.gov/pubmed/34946622
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https://doaj.org/article/24d498af424d4ac98892b5e3ea3dd2d1
Volume 26
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