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Updated: May 6, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Stereospecific synthesis of a twinned alanine ester
Jik Chin1, Soon Ho Kwon, Kimia Moozeh
1Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada. jchin@chem.utoronto.ca.
Abstract:
Reaction between 1,2-bis(2-hydroxyphenyl)-ethylenediamine (hpen) and methyl pyruvate gives the diaza-Cope rearrangement product with good yield and excellent stereospecificity. The product containing two chiral quaternary carbon centers is characterized by high performance liquid chromatography and X-ray crystallography. DFT computation provides insight into why the diaza-Cope rearrangement takes place readily with methyl pyruvate but not with other ketones like acetone and substituted acetophenones.
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