Journal ArticleDOI
Highly selective ring opening of epoxides with silicon tetrafluoride: Preparation of fluorohydrins
Makoto Shimizu,Hirosuke Yoshioka +1 more
TLDR
In this paper, the transformation of epoxides into fluorohydrins with silicon tetrafluoride was described, and a region, stereo-, and chemoselective transformation was described.About:
This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 40 citations till now. The article focuses on the topics: Silicon tetrafluoride.read more
Citations
More filters
Journal ArticleDOI
Enantioselective Ring Opening of Epoxides with Silicon Tetrachloride in the Presence of a Chiral Lewis Base.
Journal ArticleDOI
Beyond the Balz-Schiemann reaction: the utility of tetrafluoroborates and boron trifluoride as nucleophilic fluoride sources.
TL;DR: The development by Ohmori and co-workers of a fluorinative variant of the Mitsunobu reaction, involving the electrooxidative generation and subsequent thermal decomposition of alkoxytriphenylphosphonium tetrafluoroborates, allowing for the conversion of alcohols to the corresponding alkyl fluorides with inversion of configuration.
Journal ArticleDOI
Enantioselective Ring Opening of Epoxides with Silicon Tetrachloride in the Presence of a Chiral Lewis Base: Mechanism Studies
TL;DR: The enantioselective ring opening of meso- epoxides with silicon tetrachloride under catalysis by chiral phos- phoramides affords enantiomerically enriched chloro- hydrins in excellent yields as discussed by the authors.
Journal ArticleDOI
Tetrabutylammonium dihydrogentrifluoride: an efficient catalyst for regio and stereoselective conversion of epoxides to fluorohydrins under solid-liquid phase-transfer catalysis conditions.
Dario Landini,Michele Penso +1 more
TL;DR: Tetrabutylammonium dihydrogentrifluoride is an efficient and easy-to-handle hydrofluorinating agent in the ring-opening reaction of oxiranes to give good or excellent yields of fluorohydrins under solid-liquid PTC conditions.
Journal ArticleDOI
Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
Hideaki Yoshino,Kazuhiko Matsumoto,Rika Hagiwara,Yasuhiko Ito,Koichiro Oshima,Seijiro Matsubara +5 more
TL;DR: In this paper, an ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF) 2.3 ), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.
References
More filters
Journal ArticleDOI
Glycosylation using glucopyranosyl fluorides and silicon-based catalysts. Solvent dependency of the stereoselection
TL;DR: The title glycosylation method is economical and operationally simple as mentioned in this paper, and the steric course is highly influenced by the nature of the reaction media, which is the most common reaction media used in glycolysis.
Journal ArticleDOI
Base-catalyzed Rearrangement of Epoxides
Journal ArticleDOI
Synthesis of 2β-fluoro-1α-hydroxyvitamin D3
TL;DR: 2β-fluoro-1α-hydroxyvitamin D 3 (3 ) was prepared from 1,2α-epoxy-cholest-5-en-3β-yl tetrahydropyranyl ether( 1a via 2βfluorocholest 5-ene 1α, 3β-diol( 2 ).
Journal ArticleDOI
Nouvelle voie de synthese d'acides amines monofluores
A. I. Ayi,W. Remli,Roger Guedj +2 more
TL;DR: In this paper, the ring opening of the glycidonitriles (IIa-e) by HF/pyridine leads to the fluorocyanohydrins (IIIa-E), which upon acidic hydrolysis afford the βp-fluoro-α-amino acids (Va-e).