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Regio- and stereoselective microwave-assisted synthesis of 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones

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Chiral symmetrical alk-2-yne-1,4-diols have been stereoselectively transformed into 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin- 2-ones, which are precursors of quaternary α-amino β-hydroxy acids. The key step was the cyclization of the bis(tosylcarbamates) of 2- phenylalk-2-yne-1,4-diols, easily obtained from the starting chiral diols. These cyclizations were accomplished with complete regioselectivity and up to 92:8 dr in the presence of catalytic amounts of Ni(0) or Pd (II) derivatives under microwave heating.

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AMADOR PALOMAR, Marta, ARIZA PIQUER, Xavier, BOYER, Jérémie, D'ANDREA RODRÍGUEZ-VIDA, Lucía, GARCÍA GÓMEZ, Jordi, GRANELL SANVICENTE, Jaime ramón. Regio- and stereoselective microwave-assisted synthesis of 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones. _Tetrahedron Letters_. 2010. Vol. 51, núm. 6, pàgs. 935-938. [consulta: 24 de gener de 2026]. ISSN: 0040-4039. [Disponible a: https://hdl.handle.net/2445/48627]

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