Preparation and supporting on solid phase of chiral auxiliary (S)–4–(4–hydroxybenzyl)oxazolidin–2–one from L–tyrosinol assisted by Microwaves

Adriana Cruz¹ and Ignacio A. Rivero^{1,2 *}

¹ Centro de Graduados e Investigación en Química, Instituto Tecnológico de Tijuana. C.P. 1166. Tijuana, B.C. 22000, México.

² Instituto Nacional de Investigaciones Nucleares, Departamento de Química. Carretera México Toluca S/N, La Marquesa, Ocoyoacac, México, D.F. C.P. 52750. ^*Responsible author: 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 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.

Resumen

En este trabajo se reporta la preparación del nuevo auxiliar quiral de tipo oxazolidinona, (S)–(4–hidroxibencil)–1,3–oxazolidin–2–ona 4 que fue preparado a partir del L–tirosinol utilizando diferentes metodologías, con rendimientos que fluctúan en un intervalo de 23–80 %, dependiendo del método. El compuesto 4 fue preparado en solución, protegidos con el grupo benciloxi en el hidroxilo fenólico 5a, para llevar a cabo la optimización de la síntesis en fase sólida de 5b–5d. Los auxiliares quirales 5a y 5b fueron adicionados en solución a un sistema α, β–insaturado, obteniéndose a la (S)–4–(4–(benciloxi)bencil)–1,3–oxazolidin–2–ona 6, mientras que en fase sólida se observó la formación del compuesto 6b. Estas reacciones fueron activadas con microondas. Todos los compuestos fueron caracterizados mediante RMN (¹H y ¹³C), IR y EM.

Palabras Claves: Oxazolidinonas, auxiliares quirales, síntesis en fase sólida.

Acknowledgments

We gratefully acknowledge support for this project by Consejo Nacional de Ciencia y Tecnología, México (CONACyT, GRANT No. SEP–201–47835), Dirección General de Educación Tecnológica, México (DGEST) and Institute of Chemistry from National Autonomus University of México. Adriana Cruz thanks to CONACyT for a graduate fellowship.

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