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  • Title: Ruthenium-catalyzed reactions of 1-cyclopropyl-2-propyn-1-ols with anilines and water via allenylidene intermediates: selective preparation of tri- and tetrasubstituted conjugated enynes.
    Author: Yamauchi Y, Onodera G, Sakata K, Yuki M, Miyake Y, Uemura S, Nishibayashi Y.
    Journal: J Am Chem Soc; 2007 Apr 25; 129(16):5175-9. PubMed ID: 17391034.
    Abstract:
    Ruthenium-catalyzed efficient preparation of the conjugated enynes can be carried out in the reactions of 1-cyclopropyl-2-propyn-1-ols with nitrogen- and oxygen-centered nucleophiles such as anilines and water in the presence of a catalytic amount of sulfur-bridged diruthenium complexes. The use of such complexes as catalysts realizes the completely stereoselective preparation of tri- and tetrasubstituted conjugated enynes, where ruthenium-allenylidene complexes work as key intermediates. The direct attack of nucleophiles on a cyclopropane ring connected to an allenylidene ligand is a key step to obtain the enynes stereoselectively.
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