Efficient asymmetric synthesis of unnatural beta-amino acids

Citation
C. Bolm et al., Efficient asymmetric synthesis of unnatural beta-amino acids, SYNTHESIS-S, (11), 2001, pp. 1719-1730
Citations number
87
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
0039-7881 → ACNP
Issue
11
Year of publication
2001
Pages
1719 - 1730
Database
ISI
SICI code
0039-7881(200108):11<1719:EASOUB>2.0.ZU;2-D
Abstract
The simple and highly enantioselective methanolysis of cyclic meso-anhydrid es mediated by cinchona alkaloids leads to a broad variety of dicarboxylic acid mono-methyl esters with up to 99% ee. From these products, unnatural A f-protected P-amino esters can be obtained by means of Curtius degradation of the corresponding acyl azides. Subsequent cleavage of the protecting gro ups leads to the free beta -amino acids in excellent yields, By enantiomer differentiating opening of racemic anhydrides, synthetically highly useful regioisomeric amino acid esters become readily available.