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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
J. Mex. Chem. Soc vol.51 no.4 Ciudad de México oct./dic. 2007
Article
Efficient and Practical Synthesis of syn- and anti-β,Υ-Dihydroxyphosphonates Derived from (S)-Mandelic Acid
Haydée Rojas-Cabrera, Joana Ochoa-Morales, Emanuel Hernández-Núñez, Mario Fernández Zertuche and Mario Ordóñez*
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001. 62209 Cuernavaca, Morelos, México. E-mail: palacios@ciq.uaem.mx
Recibido el 25 de octubre de 2007
Aceptado el 12 de diciembre de 2007
Abstract
A new efficient and practical synthesis of syn- and anti-β,Υ-dihydroxyphosphonates 1 and 2 was developed in high diastereoselectivity via reduction of β-ketophosphonates readily obtained from (S)-mandelic acid. An example of "diastereoselective 1,2-induction" is showed and a mechanistic model to explain the stereochemical outcome is proposed. Assignment of the configuration at the new stereogenic centers was achieved by 1H NMR spectral data of their corresponding acetonides.
Key words: Diastereoselective 1,2-induction, diastereoselective reduction, β,Υ-dihydroxyphosphonates, β-ketophosphonates, (S)-mandelic acid.
Resumen
Se describe una nueva síntesis eficiente y práctica de syn- y anti-β,Υ-dihidroxifosfonatos 1 y 2 mediante la reducción diastereoselectiva de β-cetofosfonatos fácilmente preparados a partir de ácido (S)-mandélico. Esta metodología representa un ejemplo de inducción "diastereoselectiva 1,2" y se propone un modelo mecanístico para explicar la alta diastereoselectividad. La configuración absoluta del nuevo centro estereogénico se llevó a cabo mediante el análisis de los espectros de RMN de 1H de sus correspondientes acetales cíclicos.
Palabras clave: Inducción diastereoselectiva-1,2, reducción diastereoselectiva, β,Υ-dihidroxifosfonatos, β-cetofosfonatos, ácido (S)-mandélico.
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Acknowledgements
We gratefully acknowledge to CONACYT-Mexico for financial support via grant 41657-Q and 62271-Q and graduate a fellowship to H.R.C. (170296). We also thank Victoria Labastida and Blanca E. Domínguez for their valuable technical support for the obtention of the MS and NMR spectra, respectively.
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