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 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.
Clariant France, Usine de Lamotte, LRA, 60350 Trosly Breuil, France.
Muriel
M
Albalat-Serradeil
Géraldine
G
Primazot
Didier
D
Wilhelm
Jean-Claude
JC
Vallejos
Nicolas
N
Vanthuyne
Christian
C
Roussel
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D000096:Acetone / Q000737:chemistry; D000097:Acetonitriles / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000737:chemistry; D006865:Hydrogenation; D006868:Hydrolysis; D010084:Oxidation-Reduction; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D000097:Acetonitriles; D000447:Aldehydes; D000588:Amines; D005663:Furans; D012997:Solvents; D000096:Acetone; C018674:tetrahydrofuran