2802-98-4Relevant articles and documents
Electrophilic Fluorination with N-Fluoroquinuclidinium Fluoride
Banks, R. E.,Boisson, R. A. Du,Tsiliopoulos, E.
, p. 461 - 466 (1986)
N-Fluoroquinuclidinium fluoride (NFQNF), obtainable in ca. 90percent yield by direct low-temperature liquid-phase fluorination of quinuclidine, has been used to deliver 'positive' fluorine to carbanionic sites in a number of organic substrates.
A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides
Huang, Zhongxing,Low, Kam-Hung,Zhang, Suihan,Zheng, Yin,Zi, Weiwei
supporting information, p. 1951 - 1961 (2022/02/09)
Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon-halogen or carbon-carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol- or pipecolinol-derived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.
Methods for synthesis of dicarbamate compounds and intermediates in the formation thereof
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Page/Page column 7, (2008/06/13)
Disclosed is a method of making 2-substituted-2-halo-1,3-propanediols via reduction of corresponding malonate compounds. Also disclosed is a method of making 2-substituted-2-halo-1,3-dicarbamate compounds (such as halo derivatives of felbamate, including fluorofelbamate) via reduction of malonate compounds, followed by carbamoylation. Reduction of the malonate compounds is carried out using an electrophilic hydride reagent.
Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid
Fukuyama, Yasuaki,Matoishi, Kaori,Iwasaki, Masakazu,Takizawa, Eiji,Miyazaki, Mamoru,Ohta, Hiromichi,Hanzawa, Satoshi,Kakidani, Hitoshi,Sugai, Takeshi
, p. 1664 - 1666 (2007/10/03)
A preparative-scale asymmetric synthesis of (R)-α-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl α-bromophenylacetate, α-fluorophenylmalonic acid dipotassium salt was prepared in three steps (54% yield), including nucleophilic substitution by the fluoride ion as the keystep. Both the purified form and crude preparation of arylmalonate decarboxylase in E. coli worked well on this substrate, and (R)-α-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.
