Publication

Hydroxy- and carboxy-substituted allylsilanes. A simple and stereoselective method of preparation

Manfred Schlosser
1997
Journal Articles

Abstract

When treated with 2 equiv of a BuLi/KOCMe3 mixt., terminal olefins carrying unprotected OH or CO2H groups generate allylmetal intermediates which are trapped with Me3SiCl to afford functionalized (Z-2-alkenyl)trimethylsilanes. E.g., treating CH2:CHMeCO2H with 2 equiv BuLi/KOCMe3 in THF followed by Me3SiCl gave 52% E-Me3SiCH2CH:CMeCO2H. One equivalent of the superbasic reagent suffices if the unsatd. alcs. are first protected as acetals before being subjected to the metalation/silylation/hydrolysis sequence. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/080e330c-5c23-49db-be46-81bf86aabd06

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Manfred Schlosser
1997
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/080e330c-5c23-49db-be46-81bf86aabd06

About this result

Related concepts (5)

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

Carbanion

In organic chemistry, a carbanion is an anion in which carbon is negatively charged. Formally, a carbanion is the conjugate base of a carbon acid: where B stands for the base. The carbanions formed from deprotonation of alkanes (at an sp3 carbon), alkenes (at an sp2 carbon), arenes (at an sp2 carbon), and alkynes (at an sp carbon) are known as alkyl, alkenyl (vinyl), aryl, and alkynyl (acetylide) anions, respectively.

Alkane

In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula . The alkanes range in complexity from the simplest case of methane (), where n = 1 (sometimes called the parent molecule), to arbitrarily large and complex molecules, like pentacontane () or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane ().