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.

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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