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

✍ Scribed by Marta Amador; Xavier Ariza; Jérémie Boyer; Lucia D’Andrea; Jordi Garcia; Jaume Granell

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
588 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

Quaternary a-amino acids a b s t r a c t Chiral symmetrical alk-2-yne-1,4-diols have been stereoselectively transformed into 5-alkyl-4-alkenyl-4phenyl-1,3-oxazolidin-2-ones, which are precursors of quaternary a-amino b-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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