Preparation and supporting on solid phase of chiral auxiliary (S)-4-(4-hydroxybenzyl)oxazolidin-2-one from L-tyrosinol assisted by Microwaves
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.
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| Main Authors: | , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedad Química de México A.C.
2009
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| Online Access: | http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S1870-249X2009000300006 |
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