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
Publication type: Journal Article
Publication date: 2019-09-30
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31566387
Organic Chemistry
Abstract
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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12
Total citations:
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Citations from 2024:
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(25%)
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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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RIS
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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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BibTex (up to 50 authors)
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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}
}
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MLA
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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.