Journal of Organic Chemistry

, том 84 , издание 21 , страницы 13824-13831

Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives

Тип публикации: Journal Article

Дата публикации: 2019-09-30

American Chemical Society (ACS)

Journal of Organic Chemistry

SCImago Q2

WOS Q1

БС1

SJR: 0.604

CiteScore: 5.8

Impact factor: 3.3

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b02021

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PubMed ID: 31566387

Organic Chemistry

Краткое описание

A correlation between the equilibrium ratio of tautomeric products generated by the asymmetric Michael reactions of cyclic carbon acids with β,γ-unsaturated α-keto esters and the chemical shift of the α-proton in starting nucleophilic substrates was revealed which makes equilibration predictable. New tetrahydropyran-fused benzo[a]phenazins were enantioselectively (up to 99% ee) synthesized from β,γ-unsaturated α-keto esters and benzo[a]phenazin-5-ol, a powerful anti-cancer agent sAJM589. Facile recyclability of catalyst Ia in the catalytic reactions was demonstrated.

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Tukhvatshin R. S. et al. Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13824-13831.

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Tukhvatshin R. S., Kucherenko A., Nelyubina Y. V., Zlotin S. G. Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives // Journal of Organic Chemistry. 2019. Vol. 84. No. 21. pp. 13824-13831.

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TY - JOUR

DO - 10.1021/acs.joc.9b02021

UR - https://doi.org/10.1021/acs.joc.9b02021

TI - Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives

T2 - Journal of Organic Chemistry

AU - Tukhvatshin, Rinat S

AU - Kucherenko, Alexander

AU - Nelyubina, Yulia V.

AU - Zlotin, Sergei G

PY - 2019

DA - 2019/09/30

PB - American Chemical Society (ACS)

SP - 13824-13831

IS - 21

VL - 84

PMID - 31566387

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2019_Tukhvatshin,

author = {Rinat S Tukhvatshin and Alexander Kucherenko and Yulia V. Nelyubina and Sergei G Zlotin},

title = {Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {sep},

url = {https://doi.org/10.1021/acs.joc.9b02021},

number = {21},

pages = {13824--13831},

doi = {10.1021/acs.joc.9b02021}

}

MLA

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MLA Скопировать

Tukhvatshin, Rinat S., et al. “Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[a]phenazin-5-ol Derivatives.” Journal of Organic Chemistry, vol. 84, no. 21, Sep. 2019, pp. 13824-13831. https://doi.org/10.1021/acs.joc.9b02021.

Издатель

American Chemical Society (ACS)

Журнал

Journal of Organic Chemistry

SCImago Q2

WOS Q1

БС1

SJR

0.604

CiteScore

5.8

Impact factor