Synthesis of α-Cyano-β-fluoro-α-hydroxyesters
- 1 September 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (17), 2389-2395
- https://doi.org/10.1080/00397919308011124
Abstract
The ring opening fluorination of glycidic gem-cyanoesters was achieved by action of pyridine polyhydrofluoride at 25°C in dichloromethane. The regioselective nucleophilic substitution reaction allows the synthesis of a new class of fluorohydrins with OH, CN and CO2R on the same carbon atom.Keywords
This publication has 7 references indexed in Scilit:
- An efficient synthesis of 3′-fluoro-3′-deoxythymidene (FLT)Tetrahedron Letters, 1992
- Tetrabutylammonium dihydrogentrifluoride: an efficient catalyst for regio and stereoselective conversion of epoxides to fluorohydrins under solid-liquid phase-transfer catalysis conditions.Tetrahedron Letters, 1990
- Ouverture regioselective des expoxydes cis et trans derives de l'isophorol et des composes acycles correspondants par le difluorhydrate de trimethylamine Me3N, 2HF)Journal of Fluorine Chemistry, 1990
- Highly selective ring opening of epoxides with silicon tetrafluoride: Preparation of fluorohydrinsTetrahedron Letters, 1988
- Regioselective opening of simple epoxides with diisopropylamine trihydrofluorideThe Journal of Organic Chemistry, 1988
- Facile Epoxidation of Alumina-Supported Electrophilic Alkenes and Montmorillonite-Supported Electrophilic Alkenes with Sodium HypochloriteSynthesis, 1987
- Synthetic Methods and Reactions.43. Preparation of Fluorohydrins from Epoxides with Pyridinium Poly‐hydrogen FluorideIsrael Journal of Chemistry, 1978