Synthesis of Tetrastilbenylmethanes by Wittig−Horner Reactions

Kim, Soungkyoo; Seus, Peter; Meier, Herbert

doi:10.1002/ejoc.200300707

Cited by 6 publications

(1 citation statement)

References 30 publications

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“…14 Moreover, 5-chloro-3-methyl-1-phenylpyrazole-4carboxaldehyde, which is used as starting material in the present study, possesses a halogen and aldehyde function in an ortho relationship and is a potential candidate for various organic transformations. 15,16 A plethora of chemical methods have been reported for the formation of CQC bonds, which include Julia olefination, 17 Peterson olefination, 18 Ramberg-Backlund reaction, 19 Wittig reaction, 20 Wadsworth-Emmons reaction, 21 Wittig-Horner Reaction 22 and Knoevenagel condensation. 23 The Knoevenagel condensation is a facile and versatile method for the formation of carbon-carbon double bonds, with numerous applications in the synthesis of fine chemicals, 24 hetero-Diels-Alder reactions 25 and in the synthesis of carbocyclic as well as heterocyclic compounds of biological significance.…”

Section: Introductionmentioning

confidence: 99%

P2O5/SiO2 as an efficient heterogeneous catalyst for the synthesis of heterocyclic alkene derivatives under thermal solvent-free conditions

Siddiqui

Khan

2013

Catal. Sci. Technol.

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Section: Introductionmentioning

confidence: 99%

P2O5/SiO2 as an efficient heterogeneous catalyst for the synthesis of heterocyclic alkene derivatives under thermal solvent-free conditions

Siddiqui

Khan

2013

Catal. Sci. Technol.

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Wittig Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The synthesis of an olefin from the reaction between a carbonyl compound (aldehyde or ketone) and a phosphonium ylide, via either a betaine and/or oxaphosphetane intermediate is generally known as the Wittig reaction. Occasionally, it is also referred to as the Wittig alkenylation or Wittig process. The extension of this reaction by the application of a phosphine oxide carbanion, instead of a phosphonium ylide is known as the Horner reaction or Wittig Horner reaction, while the preparation of olefin from a phosphonate carbanion is commonly referred to as the Horner–Wadsworth–Emmons olefination. Several other extensions of this reaction have been addressed. All the reaction steps of the Wittig reaction have been discussed. The reversible process to give the carbonyl compound and phosphorane is also possible, and such reversible reaction is known as the retro ‐Wittig reaction. The most important feature of the Wittig reaction is probably the easy control of stereochemistry of olefins (i.e., either Z ‐ or E ‐configuration). It has been observed that ultimate configuration of olefins depends on many factors, such as the structure of phosphoranes, the base and the solvent used, the concentration of ylide, and the reaction temperature. In particular, the Z ‐selectivity from nonstabilized ylides can be further enhanced by replacement of the phenyl group in triphenylphosphane moiety with either a 2‐pyridyl or 2‐furyl group. It has been reported that even the replacement of one phenyl ring by a pyridyl group can apparently increase the Z ‐selectivity without affecting the yields of olefins. It has been reported that E ‐olefin is the major product in the protic solvent, whereas Z ‐olefin predominates in the Wittig reactions when carried out in aprotic media. Other facets of the Wittig reaction have also been discussed, which include, application of the catalysts and the enhancement of reactivity in organic solvent by the application of a phase‐transfer catalyst or promotion of the reaction by photochemical or microwave irradiation. This reaction has very wide applications in organic synthesis, such as transformation of unprotected carbohydrates and preparation of artificial carbon‐linked (1,6)‐oligosaccharides.

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A Practical Method to Stereospecifically Synthesize trans‐Stilbene Derivatives

Jian

Sun

et al. 2011

Chin. J. Chem.

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A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane (BTMS), which was driven by tetrabutylammonium fluoride (TBAF) in THF. At the same time a plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. Also this method was employed to synthesize three precursors of natural products with excellent yields, which demonstrated that this method is much efficient and practical in the synthesis of some natural products.

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Synthesis of Tetrastilbenylmethanes by Wittig−Horner Reactions

Cited by 6 publications

References 30 publications

P2O5/SiO2 as an efficient heterogeneous catalyst for the synthesis of heterocyclic alkene derivatives under thermal solvent-free conditions

P2O5/SiO2 as an efficient heterogeneous catalyst for the synthesis of heterocyclic alkene derivatives under thermal solvent-free conditions

Wittig Reaction

A Practical Method to Stereospecifically Synthesize trans‐Stilbene Derivatives

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