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

Author(s) Gebauer, K.; Reuß, F.; Spanka, M.; Schneider, C.
Journal Org Lett
Date Published 2017 Aug 15
Abstract

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 10.1021/acs.orglett.7b02185
ISSN 1523-7052
Citation Gebauer K, Reuß F, Spanka M, Schneider C. Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation. Org Lett. 2017.

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