Baur, Markus A. and Riahi, Abdelkhalek and Henin, Françoise and Muzart, Jacques (2003) Catalytic asymmetric protonation of fluoro-enolic species: access to optically active 2-fluoro-1-tetralone. TETRAHEDRON-ASYMMETRY, 14 (18). pp. 2755-2761. ISSN 0957-4166
Full text not available from this repository. (Request a copy)Abstract
Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, (S)-(-)-2-fluoro-1-tetralone with up to 65% enantiomeric excess was obtained using quinine as the chiral base and Pd/C type 807104 from Merck as the heterogeneous catalyst. (C) 2003 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHASE-TRANSFER CATALYSIS; N-FLUOROAMMONIUM SALTS; BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; CINCHONA ALKALOIDS; ELECTROPHILIC FLUORINATION; NAPROXEN DERIVATIVES; AMMONIUM-SALTS; DECARBOXYLATION; KETOESTERS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 28 Jul 2021 11:14 |
| Last Modified: | 28 Jul 2021 11:14 |
| URI: | https://pred.uni-regensburg.de/id/eprint/38600 |
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