Enzyme-mediated synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid

Antonio Salgado; Annelies Eeckhaut; Norbert De Kimpe; Johan Van der Eycken

doi:10.3390/ecsoc-4-01804

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A Convenient Synthesis of cis-3-Hydroxy-L-Proline

Enzyme-mediated synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid

Antonio Salgado

¹,

Annelies Eeckhaut

¹,

Norbert De Kimpe

^{*

1},

Johan Van der Eycken

¹ Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, B-9000 Ghent, Belgium
² Laboratory for Organic and Bio-organic Synthesis, Faculty of Sciences, Ghent University, Krijgslaan 281, B-9000 Ghent, Belgium.

Published: 11 September 2000 by MDPI in The 4th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-4-01804

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. Via a Curtius type reaction with DPPA this compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid.

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Antonio Salgado

Annelies Eeckhaut

Norbert De Kimpe

Johan Van der Eycken