Preparation and supporting on solid phase of chiral auxiliary (s)-4-(4- hydroxybenzyl)oxazolidin-2-one from l-tyrosinol assisted by microwaves Report as inadecuate




Preparation and supporting on solid phase of chiral auxiliary (s)-4-(4- hydroxybenzyl)oxazolidin-2-one from l-tyrosinol assisted by microwaves - Download this document for free, or read online. Document in PDF available to download.

Ignacio A. Rivero ;Journal of the Mexican Chemical Society 2009, 53 (3)

Author: Adriana Cruz

Source: http://www.redalyc.org/


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Journal of the Mexican Chemical Society ISSN: 1870-249X editor.jmcs@gmail.com Sociedad Química de México México Cruz, Adriana; 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 Journal of the Mexican Chemical Society, vol.
53, núm.
3, julio-septiembre, 2009, pp.
120-125 Sociedad Química de México Distrito Federal, México Available in: http:--www.redalyc.org-articulo.oa?id=47512154006 How to cite Complete issue More information about this article Journals homepage in redalyc.org Scientific Information System Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Non-profit academic project, developed under the open access initiative J.
Mex.
Chem.
Soc.
2009, 53(3), 120-125 © 2009, Sociedad Química de México ISSN 1870-249X Article Preparation and supporting on solid phase of chiral auxiliary (S)-4-(4hydroxybenzyl)oxazolidin-2-one from L-tyrosinol assisted by Microwaves Adriana Cruz1 and Ignacio A.
Rivero1,2* 1 2 Centro de Graduados e Investigación en Química, Instituto Tecnológico de Tijuana.
C.P.
1166.
Tijuana, B.C.
22000, México. Instituto Nacional de Investigaciones Nucleares, Departamento de Química.
Carretera México Toluca S-N, La Marquesa, Ocoyoacac, México, D.F.
C.P.
52750, e-mail: irivero@tectijuana.mx Received June 4, 2009; accepted August 11, 2009 Abstract.
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 o...





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