Journal of Organic Chemistry p. 13824 - 13831 (2019)
Update date:2022-08-03
Topics:
Tukhvatshin, Rinat S.
Kucherenko, Alexander S.
Nelyubina, Yulia V.
Zlotin, Sergei G.
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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