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

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 obtain...

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Bibliographic Details
Published in:Tetrahedron letters 2010-02, Vol.51 (6), p.935-938
Main Authors: Amador, Marta, Ariza, Xavier, Boyer, Jérémie, D’Andrea, Lucia, Garcia, Jordi, Granell, Jaume
Format: Article
Language:English
Subjects:
1,4-Diols
Catalysis
Catàlisi
Estereoquímica
Microones
Microwave-assisted synthesis
Microwaves
Nickel
Nickel catalysts
Níquel
Palladium
Palladium catalysts
Pal·ladi (Element químic)
Quaternary α-amino acids
Stereochemistry
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.12.036