Baur, Markus A. ; Riahi, Abdelkhalek ; Hénin, Françoise ; Muzart, Jacques
Alternative Links zum Volltext:DOIVerlag
| Dokumentenart: | Artikel |
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| Titel eines Journals oder einer Zeitschrift: | Tetrahedron: Asymmetry |
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| Verlag: | PERGAMON-ELSEVIER SCIENCE LTD |
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| Ort der Veröffentlichung: | OXFORD |
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| Band: | 14 |
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| Nummer des Zeitschriftenheftes oder des Kapitels: | 18 |
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| Seitenbereich: | S. 2755-2761 |
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| Datum: | 2003 |
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| Institutionen: | Chemie und Pharmazie > Institut für Anorganische Chemie |
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| Identifikationsnummer: | | Wert | Typ |
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| 10.1016/S0957-4166(03)00585-8 | DOI |
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| Stichwörter / Keywords: | PHASE-TRANSFER CATALYSIS; N-FLUOROAMMONIUM SALTS; BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; CINCHONA ALKALOIDS; ELECTROPHILIC FLUORINATION; NAPROXEN DERIVATIVES; AMMONIUM-SALTS; DECARBOXYLATION; KETOESTERS; |
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| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
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| Status: | Veröffentlicht |
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| Begutachtet: | Ja, diese Version wurde begutachtet |
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| An der Universität Regensburg entstanden: | Ja |
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| Dokumenten-ID: | 72070 |
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Zusammenfassung
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, ...
Zusammenfassung
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.
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