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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. / Ponomarev, K. Yu; Mozhaitsev, E. S.; Li-Zhulanov, N. S. et al.

In: Russian Chemical Bulletin, Vol. 73, No. 8, 08.2024, p. 2248-2260.

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

Harvard

Ponomarev, KY, Mozhaitsev, ES, Li-Zhulanov, NS, Okhina, AA, Nefedov, AA, Rogachev, AD, Suslov, EV, Dalinger, AI, Vatsadze, SZ, Volcho, KP & Salakhutdinov, NF 2024, '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, vol. 73, no. 8, pp. 2248-2260. https://doi.org/10.1007/s11172-024-4346-z

APA

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. (2024). 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, 73(8), 2248-2260. https://doi.org/10.1007/s11172-024-4346-z

Vancouver

Ponomarev KY, Mozhaitsev ES, Li-Zhulanov NS, Okhina AA, Nefedov AA, Rogachev AD et al. 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 Aug;73(8):2248-2260. doi: 10.1007/s11172-024-4346-z

Author

Ponomarev, K. Yu ; Mozhaitsev, E. S. ; Li-Zhulanov, N. S. et al. / The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes. In: Russian Chemical Bulletin. 2024 ; Vol. 73, No. 8. pp. 2248-2260.

BibTeX

@article{2570a53554774025922d0e2ebf434d6c,
title = "The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes",
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.",
keywords = "addition, asymmetric organocatalysis, benzaldehydes, bispidine, diethylzinc, l-amino acids, monoterpenoids",
author = "Ponomarev, {K. Yu} and Mozhaitsev, {E. S.} and Li-Zhulanov, {N. S.} and Okhina, {A. A.} and Nefedov, {A. A.} and Rogachev, {A. D.} and Suslov, {E. V.} and Dalinger, {A. I.} and Vatsadze, {S. Z.} and Volcho, {K. P.} and Salakhutdinov, {N. F.}",
note = "The study was performed within the framework of the research and development plan of the N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, and Novosibirsk State University.",
year = "2024",
month = aug,
doi = "10.1007/s11172-024-4346-z",
language = "English",
volume = "73",
pages = "2248--2260",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "8",

}

RIS

TY - JOUR

T1 - The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes

AU - Ponomarev, K. Yu

AU - Mozhaitsev, E. S.

AU - Li-Zhulanov, N. S.

AU - Okhina, A. A.

AU - Nefedov, A. A.

AU - Rogachev, A. D.

AU - Suslov, E. V.

AU - Dalinger, A. I.

AU - Vatsadze, S. Z.

AU - Volcho, K. P.

AU - Salakhutdinov, N. F.

N1 - The study was performed within the framework of the research and development plan of the N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, and Novosibirsk State University.

PY - 2024/8

Y1 - 2024/8

N2 - 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.

AB - 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.

KW - addition

KW - asymmetric organocatalysis

KW - benzaldehydes

KW - bispidine

KW - diethylzinc

KW - l-amino acids

KW - monoterpenoids

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85204462594&origin=inward&txGid=0035473206d8b5b21e924f10f34a66a0

UR - https://elibrary.ru/item.asp?id=73980078

UR - https://www.mendeley.com/catalogue/ef89cd05-d2ca-3855-80ca-e7780e75a068/

U2 - 10.1007/s11172-024-4346-z

DO - 10.1007/s11172-024-4346-z

M3 - Article

VL - 73

SP - 2248

EP - 2260

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 8

ER -

ID: 60828528