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

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 efficien...

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Veröffentlicht in:	Organic letters 2017-09, Vol.19 (17), p.4588-4591
Hauptverfasser:	Gebauer, Konrad, Reuß, Franziska, Spanka, Matthias, Schneider, Christoph
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creator	Gebauer, Konrad Reuß, Franziska Spanka, Matthias Schneider, Christoph
description	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*.
doi_str_mv	10.1021/acs.orglett.7b02185
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title	Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β‑Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation
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