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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
Resumen
ROJAS-CABRERA, Haydée et al. Efficient and Practical Synthesis of syn- and anti-β,Υ-Dihydroxyphosphonates Derived from (S)-Mandelic Acid. J. Mex. Chem. Soc [online]. 2007, vol.51, n.4, pp.237-244. ISSN 1870-249X.
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.
Palabras llave : Diastereoselective 1,2-induction; diastereoselective reduction; β,Υ-dihydroxyphosphonates; β-ketophosphonates; (S)-mandelic acid.