Abstract

CRUZ, Adriana  and  RIVERO, Ignacio A.. Preparation and supporting on solid phase of chiral auxiliary (S)-4-(4-hydroxybenzyl)oxazolidin-2-one from L-tyrosinol assisted by Microwaves. J. Mex. Chem. Soc [online]. 2009, vol.53, n.3, pp.120-125. ISSN 1870-249X.

An oxazolidinone chiral auxiliary, (S)-(4-Hydroxybenzyl)-1,3-oxazolidin-2-one 4 was prepared in 23-80 % yield from L-tyrosinol using different methodologies. In solution, compound 4 was protected with a benzyl group on the phenolic hydroxyl 5a, which allowed the optimization of the solid phase synthesis of 5b-5d. Chiral auxiliaries 5a and 5b reacted in solution with an α, β-unsaturated system to give (S)-4-(4-(benzyloxy)benzyl)-1,3-oxazolidin-2-one 6a. By contrast, in solid phase the same reaction afforded 6b. Both reactions were carried out under microwave activation. New compounds were characterized by ¹H and ¹³C NMR, infrared spectroscopy and mass spectrometry.

Keywords : Oxazolidinones; chiral auxiliaries; solid phase synthesis.