Palladium‐Catalyzed Enantioselective Four‐Component Carbonylative Dicarbofunctionalization of Internal Alkenes With 1 Atm CO
Abstract
ABSTRACT Transition metal‐catalyzed carbonylation employing CO as a C1 feedstock is fundamental for synthesizing carbonyl compounds in industrial/fine chemical synthesis. Despite the ubiquity of chiral carbonyl motifs in bioactive molecules, general methods for catalytic asymmetric carbonylation under mild conditions remain scarce, hindered by stereocontrol challenges and competing pathways. Current approaches often rely on multistep sequences or restrictive intramolecular strategies. Herein, we report palladium‐catalyzed intermolecular four‐component carbonylative dicarbofunctionalization of internal alkenes, aryl diazonium salts, and nucleophiles under 1 atm CO. This method enables simultaneous control over regio‐, diastereo‐, and enantioselectivity, efficiently constructing congested vicinal stereocenters in acyclic chiral carbonyl scaffolds. Nucleophile modularity affords diverse enantioenriched esters or ketones in high yields and stereoselectivity. The mild conditions prevent racemization of chiral carbonyls, and derivatizations highlight broad synthetic utility.
Article Details
Authors (7)
Yang Xi
Chenchen Wang
Linlin Fan
Yetong Zhang
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai China
Wei‐Hong Zhu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai China
Jingping Qu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China
Yifeng Chen
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China