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

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.
Keywords: n/a