Synthesis

Asymmetric synthesis of aliphatic α-amino and γ-hydroxy α-amino acids and introduction of a template for crystallization-induced asymmetric transformation

P Jakubec, D Berkeš, A Kolarovič, F Považanec

Index: Jakubec, Pavol; Berkes, Dusan; Kolarovic, Andrej; Povazanec, Frantisek Synthesis, 2006 , # 23 p. 4032 - 4040

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Citation Number: 11

Abstract

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.