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General Regio- and Diastereoselective Allylic C–H Oxygenation of Internal Alkenes

Kyohei Yamada, Kelvin Pak Shing Cheung, Vladimir Gevorgyan

2024Journal of the American Chemical Society42 citationsDOIOpen Access PDF

Abstract

Branched allylic esters and carboxylates are fundamental motifs prevalent in natural products and drug molecules. The direct allylic C–H oxygenation of internal alkenes represents one of the most straightforward approaches, bypassing the requirement for an allylic leaving group as in the classical Tsuji–Trost reaction. However, current methods suffer from limited scope─often accompanied by selectivity issues─thus hampering further development. Herein we report a photocatalytic platform as a general solution to these problems, enabling the coupling of diverse internal alkenes with carboxylic acids, alcohols, and other O -nucleophiles, typically in a highly regio- and diastereoselective manner.

Topics & Concepts

ChemistryAllylic rearrangementOxygenationRegioselectivityStereochemistryMedicinal chemistryOrganic chemistryCatalysisBiologyEcologyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions
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