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Zinc-Catalyzed Asymmetric Cascade Michael/Acyl Transfer Reaction between α-Hydroxy Aryl Ketones and Enynones

Hang Yan, Cui Zhang, Jiaojiao Han, Si‐Si Du, Yuan‐Zhao Hua, Min‐Can Wang, Guang‐Jian Mei, Shi‐Kun Jia

2023Organic Letters12 citationsDOI

Abstract

We described herein a neoteric enantioselective cascade Michael/acyl transfer reaction of enynones and α-hydroxy aryl ketones catalyzed by dinuclear zinc cooperative catalysis. A series of structurally diverse chiral 1,5-dicarbonyl compounds were synthesized in good yields with excellent stereoselectivities. This strategy features broad substrate scope, high atom economy, as well as enynones as efficient electrophilic acyl transfer reagents in asymmetric cascade reactions for the first time.

Topics & Concepts

ChemistryEnantioselective synthesisCatalysisArylReagentElectrophileCascadeCombinatorial chemistrySubstrate (aquarium)ZincAtom economyCascade reactionOrganic chemistryChromatographyGeologyOceanographyAlkylAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsAsymmetric Hydrogenation and Catalysis