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Synfacts 2022; 18(08): 0865
DOI: 10.1055/s-0041-1738263
DOI: 10.1055/s-0041-1738263
Metals in Synthesis
Switchable Selectivity in Pd-Catalyzed Lactonization via Ligand-Controlled Regioselective C–H Activation
Chan HS. S,
Yang J.-M,
Yu J.-Q.
*
The Scripps Research Institute, La Jolla, USA
Catalyst-Controlled Site-Selective Methylene C–H Lactonization of Dicarboxylic Acids.
Science 2022;
376: 1481-1487
DOI: 10.1126/science.abq3048
Catalyst-Controlled Site-Selective Methylene C–H Lactonization of Dicarboxylic Acids.
Science 2022;
376: 1481-1487
DOI: 10.1126/science.abq3048
Significance
The group of Yu reports a regioselective method for achieving intramolecular lactonization via palladium-catalyzed C–H activation. Notably, the selectivity can be tuned with the ligand. β-C–H activation is obtained with ligand L1, while γ-C–H activation is favoured with ligand L2.
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Comment
Both γ- and δ-lactones can be formed using ligand L1, starting from derivatives of adipic or pimelic acid, respectively. The authors demonstrated the utility of their reaction by applying it to the total synthesis of myrotheciumone A and pedicellosine.
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Publication History
Article published online:
18 July 2022
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