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

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

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Bibliographic Details
Published inAmino acids Vol. 43; no. 2; p. 687
Main Authors Albalat-serradeil, Muriel, Primazot, Géraldine, Wilhelm, Didier, Vallejos, Jean-claude, Vanthuyne, Nicolas, Roussel, Christian
Format Journal Article
LanguageEnglish
Published Vienna Springer Nature B.V 01.08.2012
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Summary:The first successful resolution of rac-[alpha]-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of [alpha]-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 [alpha]-aminoaldehyde intermediates. A racemization method of optically enriched [alpha]-aminoacetals is exemplified to allow valorisation of both enantiomers.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-011-1117-6