Publication

The mechanism of catalytic enantioselective fluorination: Computational and experimental studies

2002
Journal Articles

Abstract

A parallel orientation between the coordinated substrate enolate and a face-on naphthyl group of the TAD-DOL ligand control the stereochem. outcome of the Ti-catalyzed asym. fluorination of 1,3-dicarbonyl compds. with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanetriethylenediamine (F-TEDA). D. functional theory based quantum-mech. mol. mech. calcns. also disclose the fluorine-transfer step as occurring by a single-electron transfer. [on SciFinder (R)]

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2002
Journal Articles

Abstract

Official source

Related concepts (14)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Organozinc chemistry

Organozinc chemistry is the study of the physical properties, synthesis, and reactions of organozinc compounds, which are organometallic compounds that contain carbon (C) to zinc (Zn) chemical bonds. Organozinc compounds were among the first organometallic compounds made. They are less reactive than many other analogous organometallic reagents, such as Grignard and organolithium reagents. In 1848 Edward Frankland prepared the first organozinc compound, diethylzinc, by heating ethyl iodide in the presence of zinc metal.

Fluorine

Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reactive, as it reacts with all other elements except for the light inert gases. Among the elements, fluorine ranks 24th in universal abundance and 13th in terrestrial abundance.

Related publications (1)

The mechanism of catalytic enantioselective fluorination: Computational and experimental studies

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Parametrization of substituents: effects of fluorine and other heteroatoms on OH, NH, and CH acidities