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April 17, 2026Journal of the American Chemical Society2 citations

Enantioselective Palladium-Catalyzed Intermolecular Four-Component Acylcarbonylation of Alkenes: A Modular Approach to Chiral γ-Keto Esters

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WZWei ZhouSouthwest UniversityYXYao XiaoSouthwest UniversityJCJian ChenSouthwest University

Key Points

  • The study aims to develop a new method for synthesizing chiral γ-keto esters using palladium-catalyzed reactions.
  • Implemented palladium-catalyzed asymmetric intermolecular four-component reactions.
  • Utilized electron-rich pyridine-oxazoline ligands under mild conditions.
  • Studied the influence of the Pyox ligand on chemo- and enantioselectivity.
  • Successfully produced chiral γ-keto esters from aliphatic alkenes and styrenes.
  • Achieved good yields and enantioselectivity in the synthesis.
  • Demonstrated that the choice of ligand significantly affects reaction outcomes.

Abstract

Palladium-catalyzed asymmetric acylcarbonylation of alkenes is a straightforward strategy for preparing optically active γ-keto esters. Owing to the low reactivity of acyl-Pd(II) species toward alkenes, documented methodologies have focused on intramolecular three-component reactions. Herein, we communicate the palladium-catalyzed asymmetric intermolecular four-component acylcarbonylation of alkenes under mild conditions, enabled by electron-rich pyridine-oxazoline (Pyox) ligands. This method conforms to aliphatic alkenes and styrenes, affording chiral γ-keto esters in good yields and enantioselectivity. The design of the Pyox ligand crucially influences both the chemo- and enantioselectivity. Furthermore, the resulting products serve as valuable intermediates for synthesizing value-added fine chemicals.

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Cite This Study

Zhou et al. (2026) studied this question.

synapsesocial.com/papers/69e1cefb5cdc762e9d857ec6https://doi.org/10.1021/jacs.6c04152
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