Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

The first successful resolution of rac - α -aminoacetals via diastereoisomeric salt formation with optically pure N -protected aminoacids is reported. The absolute configuration assignment of α -aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving...

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Published inAmino acids Vol. 43; no. 2; pp. 687 - 696
Main Authors Albalat-Serradeil, Muriel, Primazot, Géraldine, Wilhelm, Didier, Vallejos, Jean-Claude, Vanthuyne, Nicolas, Roussel, Christian
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.08.2012
Springer Verlag
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Summary:The first successful resolution of rac - α -aminoacetals via diastereoisomeric salt formation with optically pure N -protected aminoacids is reported. The absolute configuration assignment of α -aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N -protection and a new efficient hydrolysis step followed by a reduction of the resulting N -protected α -aminoaldehyde intermediates. A racemization method of optically enriched α -aminoacetals is exemplified to allow valorisation of both enantiomers.
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ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-011-1117-6