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

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

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2021, Volume: 26, Number: 24, Article number : 7539, Pages count : DOI: 10.3390/molecules26247539

Tags

Bispidines; Catalysis; Chalcones; Chiral ligands; Dialkylzincs addition; Ethylation; Monoterpenoids; Natural compounds; Nickel complexes

Authors

Suslov Evgeniy V. ¹ , Ponomarev Konstantin Y. ¹ , Patrusheva Oxana S. ¹ , Kuranov Sergey O. ¹ , Okhina Alina A. ^1,2 , Rogachev Artem D. ^1,2 , Munkuev Aldar A. ¹ , Ottenbacher Roman V. ³ , Dalinger Alexander I. ⁴ , Kalinin Mikhail A. ⁴ , Vatsadze Sergey Z. ⁴ , Volcho Konstantin P. ¹ , Salakhutdinov Nariman F. ¹

Affiliations

1	Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrent’ev Av., 9, Novosibirsk, 630090, Russian Federation
2	Faculty of Natural Sciences, Novosibirsk State University, Pirogov Str., 2, Novosibirsk, 630090, Russian Federation
3	Boreskov Institute of Catalysis SB RAS, Lavrent’ev Av., 5, Novosibirsk, 630090, Russian Federation
4	Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, MSU, 1-3, Moscow, 119991, Russian Federation

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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

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.
Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones
Molecules. 2021. V.26. N24. 7539 . DOI: 10.3390/molecules26247539 WOS Scopus

Web of science	WOS:000745034900001
Scopus	2-s2.0-85121206812
OpenAlex	W4200463881