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Synthesis 2012(8): 1247-1252  
DOI: 10.1055/s-0031-1289746
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Divergent Synthetic Strategy Based on the Regioselective Reductive Ring-Opening of a Cyclic 1,2-p-Methoxybenzylidene Acetal

Pierre-Yves Géant, Jean Martínez, Lou Rocard, Xavier J. Salom-Roig*
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Université Montpellier I et II, CNRS, Place Eugène Bataillon, 34095 Montpellier, France
Fax: +33(467)144866; e-Mail: salom-roig@univ-montp2.fr;
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Publication History

Received 6 January 2012
Publication Date:
15 March 2012 (online)

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Abstract

(1S)-N,N-Dibenzyl-1-[(4R)-2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethanamine is obtained in five steps from an α-bromo­-α′-(R)-sulfinyl ketone and is used as a common intermediate for the synthesis of the p-methoxybenzyl-protected primary and secondary alcohols, (2R,3S)-3-(dibenzylamino)-2-[(4-methoxy­benzyl)oxy]butan-1-ol and (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol, respectively. These alcohols are further exploited as precursors for the synthesis of a fully protected syn-3-amino-2-hydroxybutanoic acid and an N-benzyl 2-hydroxymethyl­aziridine.

Key words

sulfoxides - diols - protecting groups - neighboring-group effects - regioselectivity

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