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• W2952847251 endingPage "1491" @default.
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• W2952847251 abstract "Abstract Chemo‐ and stereoselective transformations of 3‐hydroxy‐1,5‐allenynes 1 into a variety of new and potentially useful cyclic compounds have been achieved. Substrates bearing a silyl group at the alkyne moiety undergo purely thermal or Lewis acid catalyzed Alder‐ene type transformations into 2‐methylene‐3‐vinylcyclopent‐3‐enol derivatives 2 . When heated in the presence of a catalytic amount of PtCl 2 or PtCl 4 , these incipient cyclopentenols could be further transformed into 3‐vinylcyclopent‐2‐enones 3 . On the other hand, alkyl‐substituted 3‐hydroxy‐1,5‐allenynes proved to be stable under refluxing conditions. Nevertheless, PtCl 2 and PtCl 4 could selectively activate the alkyne moiety of these substrates toward intramolecular nucleophilic attack of the internal allene double bond to yield unprecedented 6‐methylenebicyclo[3.1.0]hexan‐3‐one derivatives 4 . With gold‐based catalysts, provided that the reaction is carried out in dichloromethane, both Au I and Au III complexes selectively activate the allene fragment of the substrates toward intramolecular nucleophilic attack of the hydroxyl group to yield 2‐ethynyl‐3,6‐dihydro‐2 H ‐pyrans 5 . Compounds of type 4 can also be formed with Au I and Au III complexes if the reaction is carried out in toluene. The reactivity of these new compounds has been partially investigated, and polycyclic ketones were obtained after oxidation under mild conditions or gold‐catalyzed cycloisomerization." @default.
• W2952847251 created "2019-06-27" @default.
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• W2952847251 date "2008-02-01" @default.
• W2952847251 modified "2023-10-18" @default.
• W2952847251 title "Alkyne versus Allene Activation in Platinum- and Gold-Catalyzed Cycloisomerization of Hydroxylated 1,5-Allenynes" @default.
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• W2952847251 doi "https://doi.org/10.1002/chem.200701522" @default.
• W2952847251 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18034446" @default.
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