Publication

Highly selective additions of hydride and organolithium nucleophiles to helical carbenium ions

Philip Pattison, Jérôme Lacour
2011
Journal Articles

Abstract

Unsymmetrical cationic [4] helicenes react with hydride or organolithium reagents and the two diastereotopic faces can be discriminated with high efficiency (dr up to and higher than 49 : 1)

Official source

https://infoscience.epfl.ch/entities/publication/5943778e-e5d1-4ac4-84d0-b2a54047a204

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Philip Pattison, Jérôme Lacour
2011
Journal Articles

Abstract

Unsymmetrical cationic [4] helicenes react with hydride or organolithium reagents and the two diastereotopic faces can be discriminated with high efficiency (dr up to and higher than 49 : 1)

Official source

https://infoscience.epfl.ch/entities/publication/5943778e-e5d1-4ac4-84d0-b2a54047a204

About this result

Related concepts (7)

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.

Gilman reagent

A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl. These reagents are useful because, unlike related Grignard reagents and organolithium reagents, they react with organic halides to replace the halide group with an R group (the Corey–House reaction). Such displacement reactions allow for the synthesis of complex products from simple building blocks. These reagents were discovered by Henry Gilman and coworkers.

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.

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