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• W1990701319 abstract "Carbonyl-tethered propargylic benzoates undergo intramolecular carbonylpropargylation upon treatment with Et2Zn in the presence of a catalytic amount of Pd0 with the formation of 2-alkynylcyclopentanol products. A ligand/solvent effect on the cis/trans selectivity (referring to the relative positions of alkynyl and OH groups) of ring-closure has been found. In a non-coordinating solvent (benzene), increasing the electron-donating ability of the phosphine ligand (while decreasing its dissociation ability) leads to an increased tendency towards the trans product. On the other hand, the combination of a coordinating solvent (THF) and PPh3, an easily dissociated phosphine, results in the exclusive formation of cis products. Experimental and computational results are compatible with a divergent behavior of an allenylethylpalladium intermediate that partitions between competitive carbonyl-addition and transmetalation pathways, each leading to a different diastereoisomer. These results also suggest that the dissociating ability of the phosphine regulates that behavior." @default.
• W1990701319 created "2016-06-24" @default.
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• W1990701319 date "2013-08-21" @default.
• W1990701319 modified "2023-10-18" @default.
• W1990701319 title "Catalyst- and Solvent-Dependent Stereodivergence in the Intramolecular Et₂Zn/Pd⁰-Promoted Carbonyl Propargylation: Mechanistic Implications" @default.
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• W1990701319 doi "https://doi.org/10.1002/chem.201301170" @default.
• W1990701319 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23963967" @default.
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