Publication

Superbases for organic synthesis

Manfred Schlosser
1988
Journal Articles

Abstract

A review with 70 refs. LICKOR mixts. of organolithium reagents and bulky potassium alcoholates allow the smooth metalation and subsequent electrophilic substitution of low acidity hydrocarbons, in particular olefins. The allylpotassium intermediates exhibit peculiar conformational preferences which can be exploited in novel stereoselective carbon-carbon linking reactions. A few syntheses of simple natural products illustrate the method. A tentative explanation is given for the superior performance of LICKOR mixts. when compared with butylpotassium. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/a8409461-e7c6-4db1-88b1-ac957e1cc82c

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Manfred Schlosser
1988
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/a8409461-e7c6-4db1-88b1-ac957e1cc82c

About this result

Related concepts (20)

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.

Grignard reagent

A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used.

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: total synthesis, semisynthesis, and methodology.

Related publications (1)

Superbases for organic synthesis

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Bayesian and Data-Efficient Strategies for the Optimization of Organic Reactions