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Synthesis 2006(23): 4032-4040
DOI: 10.1055/s-2006-950319
DOI: 10.1055/s-2006-950319
PAPER
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Synthesis of Aliphatic α-Amino and γ-Hydroxy α-Amino Acids and Introduction of a Template for Crystallization-Induced Asymmetric Transformation
Further Information
Received
21 June 2006
Publication Date:
12 October 2006 (online)
Publication History
Publication Date:
12 October 2006 (online)
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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