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The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2024, Volume: 73, Number: 8, Pages: 2248-2260 Pages count : 13 DOI: 10.1007/s11172-024-4346-z
Authors Ponomarev K.Yu. 1 , Mozhaitsev E.S. 1 , Li-Zhulanov N.S. 2 , Okhina A.A. 1,2 , Nefedov A.A. 1 , Rogachev A.D. 1 , Suslov E.V. 1 , Dalinger A.I. 3 , Vatsadze S.Z. 3 , Volcho K.P. 1 , Salakhutdinov N.F. 1
Affiliations
1 Department of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’va, 630090, Novosibirsk, Russian Federation
2 Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation
3 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Abstract: A series of bispidine conjugates bearing monoterpene moieties and either l-proline or l-phenylalanine residues was synthesized. The synthesized bispidines can catalyze asymmetric ethylation of benzaldehydes with diethylzinc. The highest enantioselectivity of the addition reaction (ee 24%) was achieved for bispidine with (–)-α-pinene and Boc-l-proline moieties.
Cite: Ponomarev K.Y. , Mozhaitsev E.S. , Li-Zhulanov N.S. , Okhina A.A. , Nefedov A.A. , Rogachev A.D. , Suslov E.V. , Dalinger A.I. , Vatsadze S.Z. , Volcho K.P. , Salakhutdinov N.F.
The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes
Russian Chemical Bulletin. 2024. V.73. N8. P.2248-2260. DOI: 10.1007/s11172-024-4346-z WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001317720800007
Scopus: 2-s2.0-85204462594
OpenAlex: W4402652305
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