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Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of ?-Methylene-?-Lactones.

ABSTRACT: The first general and regioselective Pd-catalyzed cyclocarbonylation to give ?-methylene-?-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)₂ Cl₂ as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding ?-methylene-?-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.

SUBMITTER: Ge Y

PROVIDER: S-EPMC7756850 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Ge Yao Y Ye Fei F Liu Jiawang J Yang Ji J Spannenberg Anke A Jiao Haijun H Jackstell Ralf R Beller Matthias M

Angewandte Chemie (International ed. in English) 20200917 48

The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)<sub>2</sub> Cl<sub>2</sub> as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastere ...[more]

PMID: 32573055

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