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Enantioselective transannular reactions by palladium-catalysed conjugate addition of aryl boronic acids.

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A palladium-catalyzed asymmeric conjugate addition of aryl boronic acids to medium-sized cycloalkenones followed by intramolecular aldol trapping is reported. The use of in situ formed [Pd/(QuinoxP*)] as the catalyst enables… Click to show full abstract

A palladium-catalyzed asymmeric conjugate addition of aryl boronic acids to medium-sized cycloalkenones followed by intramolecular aldol trapping is reported. The use of in situ formed [Pd/(QuinoxP*)] as the catalyst enables the synthesis of arylbicyclic scaffolds in good yields and with excellent stereocontrol (up to 7 : 1 dr, up to 99% ee). The reaction is applicable to a range of medium size ketoenone substrates and funcionalized aryl boronic acids, including heterocyclic compounds.

Keywords: boronic acids; addition aryl; conjugate addition; aryl boronic

Journal Title: Chemical communications
Year Published: 2022

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