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

Autor: Albalat-Serradeil M; Clariant France, Usine de Lamotte, LRA, 60350 Trosly Breuil, France., Primazot G, Wilhelm D, Vallejos JC, Vanthuyne N, Roussel C
Jazyk: angličtina
Zdroj: Amino acids [Amino Acids] 2012 Aug; Vol. 43 (2), pp. 687-96. Date of Electronic Publication: 2011 Oct 21.
DOI: 10.1007/s00726-011-1117-6
Abstrakt: 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.
Databáze: MEDLINE