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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

Rinat S Tukhvatshin, Alexander S Kucherenko, Yulia V Nelyubina, Sergei G Zlotin

J Org Chem. 2019 Nov 1;84(21):13824-13831.

PMID: 31566387

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2089829	sAJM589		2089-82-9	Price

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