Eine neue Aldehyd‐Synthese

Wittig, Georg; Knauss, Erhard

doi:10.1002/ange.19590710312

Cited by 31 publications

(2 citation statements)

References 2 publications

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“…In the 1950s, Levine and Wittig independently reported the preparation of (methoxymethyl) triphenylphosphonium chloride ( 2 ) and its reaction with aldehydes ( 1 ) to yield enol ethers ( 3 , Scheme a) . This reaction paired with the hydrolysis of 3 to aldehydes ( 4 ) , constituted a simple one-carbon homologation of aldehydes that has since been routinely employed in the context of natural products synthesis …”

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confidence: 99%

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

et al. 2021

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Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile twostep one-carbon homologation of aldehydes to ketones.

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confidence: 99%

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

et al. 2021

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“…2 3 4 5 In the 1950s, Levine and Wittig used methoxymethyl triphenylphosphonium chloride ( 1 ) to enable a simple homologation of aldehydes via enol ether intermediates and subsequent hydrolysis (Scheme 1 A). 6 7 In 2021, we showed that thioalkyl phosphonium salts ( 2 ) can be used for analogous aldehyde-to-ketone homologations via vinyl sulfide intermediates (Scheme 1 B). 8 We synthesized several phosphonium salts (e.g., 2a – e ) from sulfoxides, using a procedurally facile Pummerer-like process, and used the salts in olefinations with aldehydes to yield vinyl sulfides.…”

Section: Table 1 Screen Of Solvents and Brønsted And Le...mentioning

confidence: 99%

Use of Vinyl Sulfides in Fischer Indole Reactions

Pal¹,

Fragis²,

Dharavath³

et al. 2022

Synthesis

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Vinyl sulfides accessed via Wittig olefination with thioalkylphosphonium salts are used as aldehyde- or ketone surrogates in Fischer indole reactions. These vinyl sulfides react with arylhydrazines in the presence of TsOH·H2O in refluxing ethanol or dichloroethane to yield diverse 3-substituted and 2,3-disubstituted indoles or azaindoles. The utility of this chemistry is highlighted with the efficient preparation of three biomedically relevant compounds: 4-aza-melatonin, a furoindoline, and an indomethacin-like CRTh2 antagonist.

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The Wittig Reaction

Maercker

2011

Organic Reactions

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In 1953 Wittig and Geissler found that reaction of benzophenone with methylenetriphenylphosphorane gave 1,1‐diphenylethylene and triphenylphosphine oxide in almost quantitative yield; the phosphine had been prepared from triphenylmethylphosphonium bromide and phenyl lithium. The discovery led to the development of a new method for the synthesis of olefins, under the name Wittig reaction. One advantage of this new method is that the carbonyl group is replaced specifically by a carbon‐carbon double bond without the formation of isomeric olefins. In contrast, the older method of converting carbonyl compounds to olefins using the Grignard reaction usually give a mixture of isomeric olefins. Another advantage is the Wittig reaction is carried out under mild conditions. Discussions of modern techniques for the preparation of methylene phosphoranes are included in this review.

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Eine neue Aldehyd‐Synthese

Cited by 31 publications

References 2 publications

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Use of Vinyl Sulfides in Fischer Indole Reactions

The Wittig Reaction

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