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 Full article
| Journal |
Tetrahedron
ISSN: 0040-4020 |
||||||||
|---|---|---|---|---|---|---|---|---|---|
| Output data | Year: 2001, Volume: 57, Number: 14, Pages: 2781-2786 Pages count : DOI: 10.1016/S0040-4020(01)00112-0 | ||||||||
| Tags | 1-aminocyclopropane-1-carboxylic acid; enzymatic hydrolysis; Curtius rearrangement; 2,2-dimethylACC | ||||||||
| Authors |
|
||||||||
| Affiliations |
|
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. (C) 2001 Elsevier Science Ltd. All rights reserved.
Cite:
Salgado A.
, Huybrechts T.
, Eeckhaut A.
, Van der Eycken J.
, Szakonyi Z.
, Fulop F.
, Tkachev A.
, De Kimpe N.
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. 2001. V.57. N14. P.2781-2786. DOI: 10.1016/S0040-4020(01)00112-0 WOS Scopus РИНЦ OpenAlex
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. 2001. V.57. N14. P.2781-2786. DOI: 10.1016/S0040-4020(01)00112-0 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Apr 1, 2001 |
Identifiers:
| Web of science: | WOS:000167884400014 |
| Scopus: | 2-s2.0-0035795078 |
| Elibrary: | 14040342 |
| OpenAlex: | W2055878966 |