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Manipulating L-Aspartic and L-Glutamic Acids − Diastereoselective Synthesis of Enantiopure β-Amino-γ-hydroxy Acids and γ-Amino-δ-hydroxy Acids

✍ Scribed by José M. Andrés; Eva M. Muñoz; Rafael Pedrosa; Alfonso Pérez-Encabo

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
250 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Enantiopure (3__S__,4__R__)‐ and (3__S__,4__S__)‐3‐amino‐4‐hydroxyhexanoic acids and (4__S__,5__R__)‐ and (4__S__,5__S__)‐4‐amino‐5‐hydroxyheptanoic acid derivatives have been prepared by stereodivergent synthesis from L‐aspartic and L‐glutamic acids, respectively. The stereochemistry at the carbon atom attached to the amino group was determined from the starting material, but the configuration at C‐4 or C‐5 is controlled by diastereoselective alkylation with diethylzinc or ethylmagnesium bromide. The protection of the carboxylic group as OBO orthoester improved the yields in the final products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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