Enantioselective Synthesis of Tertiary [alpha]-Hydroxyketones from Unfunctionalized Ketones: Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

Aiming high: The title reaction for the synthesis of tertiary [alpha]-hydroxyketones is reported. Protected 1,2-enediol carbonates, the starting materials, were accessed from simple and readily available enol carbonates. Highly functionalized tertiary [alpha]-hydroxyketones can be obtained in high y...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-08, Vol.51 (33), p.8290-8293
Hauptverfasser: Trost, Barry M, Koller, Raffael, Schaffner, Benjamin
Format: Artikel
Sprache:eng
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Zusammenfassung:Aiming high: The title reaction for the synthesis of tertiary [alpha]-hydroxyketones is reported. Protected 1,2-enediol carbonates, the starting materials, were accessed from simple and readily available enol carbonates. Highly functionalized tertiary [alpha]-hydroxyketones can be obtained in high yield with excellent enantioselectivity using this method (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203663