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 in | Amino acids Vol. 43; no. 2; pp. 687 - 696 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Vienna
Springer Vienna
01.08.2012
Springer Verlag |
Subjects | |
Online Access | Get full text |
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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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1 |
ISSN: | 0939-4451 1438-2199 |
DOI: | 10.1007/s00726-011-1117-6 |