Abstract

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.

Keywords : Diastereoselective 1,2-induction; diastereoselective reduction; β,Υ-dihydroxyphosphonates; β-ketophosphonates; (S)-mandelic acid.

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