Asymmetric Synthesis of Aliphatic α-Amino and γ-Hydroxy α-Amino Acids and Introduction of a Template for Crystallization-Induced Asymmetric Transformation

Pavol Jakubec; Dušan Berkeš; Andrej Kolarovič; František Považanec

doi:10.1055/s-2006-950319

PAPER

Asymmetric Synthesis of Aliphatic α-Amino and γ-Hydroxy α-Amino Acids and Introduction of a Template for Crystallization-Induced Asymmetric Transformation

Pavol Jakubec, Dušan Berkeš, Andrej Kolarovič*, František Považanec
Department of Organic Chemistry, Slovak Technical University, Radlinského 9, 81237 Bratislava, Slovak Republic
Fax: +421(2)52968560; e-Mail: andrej.kolarovic@stuba.sk;

Abstract

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Abstract

The asymmetric synthesis of aliphatic α-amino and γ-hydroxy α-amino acids is described. The key step is an aza-Michael addition controlled by crystallization-induced asymmetric transformation (CIAT), affording excellent diastereomeric ratios (dr ≥96:4). Consecutive deoxygenation or stereoselective reduction (dr 99:1) furnish various α-amino and γ-hydroxy α-amino acids, respectively.

Key words

amino acids - asymmetric synthesis - Michael additions - reductions - solvent effects

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