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

Authors
Salgado, A Huybrechts, T Eeckhaut, A Van der Eycken, J Szakonyi, Z Fulop, F Tkachev, A De Kimpe, N
Citation
A. Salgado et al., 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, TETRAHEDRON, 57(14), 2001, pp. 2781-2786
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
14
Year of publication
2001
Pages
2781 - 2786
Database
ISI
SICI code
0040-4020(20010402)57:14<2781:SO(AVP>2.0.ZU;2-6
Abstract
Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarb oxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluo roethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric exces s. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1 -[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate via a Curtius type re action with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylc yclopropane-1-carboxylic acid. (C) 2001 Elsevier Science Ltd. All rights re served.