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

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 Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 21, Pages: 13824-13831 Pages count : 8 DOI: 10.1021/acs.joc.9b02021

Authors

Tukhvatshin Rinat S. ^1,2 , Kucherenko Alexander S. ¹ , Nelyubina Yulia V. ² , Zlotin Sergei G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prospect, 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, Vavilova Str, 119991 Moscow, Russian Federation

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.

Tukhvatshin R.S. , Kucherenko A.S. , 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. V.84. N21. P.13824-13831. DOI: 10.1021/acs.joc.9b02021 WOS Scopus OpenAlex

Web of science:	WOS:000494562600054
Scopus:	2-s2.0-85073202544
OpenAlex:	W2978206314

DB	Citing
OpenAlex	12
Scopus	12
Web of science	13