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Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids

Kohei Sekine, Takanori Mawatari, Tohru Yamada*

*Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan, Email: yamadachem.keio.ac.jp

K. Sekine, T. Mawatari, T. Yamada, Synlett, 2015, 26, 2447-2450.

DOI: 10.1055/s-0035-1560263 (free Supporting Information)


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Abstract

The use of a combination of silver acetate and N,N-dimethylaminopyridine enables a highly Z-selective syntheses of oxazolidin-2-ones from propargylic alcohols containing internal alkynes and phenyl isocyanate. The silver catalyst effectively activates the C≡C triple bond by acting as a π-Lewis acid to produce the corresponding oxazolidinones with high Z-selectivities.

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Key Words

silver, cyclizations, oxazolidinones, tandem reactions, isocyanates


ID: J60-Y2015