Efficient Asymmetric Synthesis of Unnatural β-Amino Acids

Carsten Bolm; Ingo Schiffers; Christian L. Dinter; Laurent Defrère; Arne Gerlach; Gerhard Raabe

doi:10.1055/s-2001-16745

SPECIALTOPIC

Efficient Asymmetric Synthesis of Unnatural β-Amino Acids

Carsten Bolm*, Ingo Schiffers, Christian L. Dinter, Laurent Defrère, Arne Gerlach, Gerhard Raabe
Institut für Organische Chemie der, RWTH Aachen, Professor-Pirlet-Strasse 1, 52056 Aachen, Germany
Fax: +49(241)8888391; e-Mail: Carsten.Bolm@oc.rwth-aachen.de;

Abstract

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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.

Key words

asymmetric ring opening - chiral methyl esters - Curtius degradation - β-amino acids - enantiomer differentiating reaction

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References

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