Synthesis of (1S)-1-amino-2, 2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2, 2, 2-trifluoroethyl) 2, 2-dimethylcyclopropane-1, 1-dicarboxylate

Abstract:

Hydrolysis of bis(2, 2, 2-trifluoroethyl) 2, 2-dimethylcyclopropane-1, 1-dicarboxylate with pig liver esterase afforded (1R)-2, 2-dimethyl-1-(2, 2, 2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2, 2, 2-trifluoroethyl-2, 2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2, 2-dimethylcyclopropane-1-carboxylic acid. © 2001 Elsevier Science Ltd.

Año de publicación:

2001

Keywords:

• 2, 2-DimethylACC
• 1-Aminocyclopropane-1-carboxylic acid
• Curtius rearrangement
• enzymatic hydrolysis

Fuente:

scopus