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Asymmetric Retro-Claisen Reaction by Synergistic Chiral Primary Amine/Palladium Catalysis
journal contributionposted on 2019-09-05, 16:34 authored by Yanfang Han, Long Zhang, Sanzhong Luo
We described herein a chiral primary amine/palladium catalyzed asymmetric retro-Claisen reaction of β-diketones with salicylic carbonates. A series of chiral α-alkylated ketones and macrolides were obtained with good yields and excellent enantioselectivities upon a sequence of decarboxylative benzylation, retro-Claisen cleavage, and enamine protonation. This strategy features broad substrate scope, mild conditions, as well as high atom economy with salicylic carbonates as the o-quinone methide precursors.
sequenceseriesdecarboxylative benzylationretro-Claisen reactionAsymmetric Retro-Claisen ReactionSynergistic Chiralsubstrate scopeatom economyquinone methide precursorschiral α- alkylated ketonesretro-Claisen cleavageAminestrategy featurescarbonatesβ- diketonesmacrolideyieldenamine protonationCatalysienantioselectivitie