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

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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, 19.09.2024, p. 2248-2260.

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

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.}",

year = "2024",

month = sep,

day = "19",

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.

PY - 2024/9/19

Y1 - 2024/9/19

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.mendeley.com/catalogue/ef89cd05-d2ca-3855-80ca-e7780e75a068/

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

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