Efficient Asymmetric Synthesis of Unnatural β-Amino Acids
- 1 January 2001
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2001 (11) , 1719-1730
- https://doi.org/10.1055/s-2001-16745
Abstract
The simple and highly enantioselective methanolysis of cyclic meso-anhydrides mediated by cinchona alkaloids leads to a broad variety of dicarboxylic acid mono-methyl esters with up to 99% ee. From these products, unnatural N-protected β-amino esters can be obtained by means of Curtius degradation of the corresponding acyl azides. Subsequent cleavage of the protecting groups leads to the free β-amino acids in excellent yields. By enantiomer differentiating opening of racemic anhydrides, synthetically highly useful regioisomeric amino acid esters become readily available.Keywords
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