Organic Letters
Organic Letters
5 years ago

Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation

Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation
Christoph Schneider, Matthias Spanka, Konrad Gebauer, Franziska Reuß
The combination of an in situ formed MnL3 complex (HL = Hacac or R(C═O)CH2CO2R) and a chiral phosphoric acid HX* allows for a fully catalytic, asymmetric synthesis of 4H-chromenes starting from 2-alkyl-substituted phenols. The aerobic oxidation toward a transient ortho-quinone methide was efficiently catalyzed by a manganese(III) species MnL3 while the ensuing Michael addition of β-dicarbonyl compounds proved to be catalyzed by a chiral manganese phosphate MnL2X*.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02185

DOI: 10.1021/acs.orglett.7b02185

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