A Divergent Synthetic Strategy Based on the Regioselective Reductive Ring-Opening of a Cyclic 1,2-p-Methoxybenzylidene Acetal - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2012

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

Résumé

Dibenzyl-1-[(4R)-2-(4-methoxyphenyl)-1,3dioxolan-4-yl]ethanamine is obtained in five steps from an abromo-a¢-(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-3amino-2-hydroxybutanoic acid and an N-benzyl 2-hydroxymethylaziridine.
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Dates et versions

hal-03468366 , version 1 (08-12-2021)

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Pierre-Yves Géant, Jean Martínez, Lou Rocard, Xavier J Salom-Roig. A Divergent Synthetic Strategy Based on the Regioselective Reductive Ring-Opening of a Cyclic 1,2-p-Methoxybenzylidene Acetal. Synthesis: Journal of Synthetic Organic Chemistry, 2012, 44 (08), pp.1247-1252. ⟨10.1055/s-0031-1289746⟩. ⟨hal-03468366⟩
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