Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

Johan Van der Eycken, Norbert De Kimpe, Annelies Eeckhaut, Antonio Salgado, Enzyme-mediated synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01804

Facebook

Twitter

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 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

Efficient allylation of 4-silyloxy quinolinium triflates and other positively charged heteroaromatic systems

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