Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to <i>C</i>‐Glycoside Amphiphiles

Ranoux, Adeline; Lemiègre, Loı̈c; Benoit, Maud; Guégan, Jean‐Paul; Benvegnu, Thierry

doi:10.1002/ejoc.200901286

Cited by 41 publications

(34 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In cases where enones or enaldehydes are produced in the olefination reaction, a 1,4-addition becomes a possibility; this includes the Michael addition [149][150][151]. Also, the combination of ring opening of cyclic hemiacetals or acetals, olefination reaction and a 1,4-addition leading to ring closure is quite common [154][155][156]. The outcome of one-pot sequences of olefination reaction-electrocyclic rearrangement can be predicted less easily.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Merza¹,

Taha²,

Thiemann³

2018

Alkenes

View full text Add to dashboard Cite

The Wittig olefination utilizing phosphoranes and the related Horner-WadsworthEmmons (HWE) reaction using phosphonates transform aldehydes and ketones into substituted alkenes. Because of the versatility of the reactions and the compatibility of many functional groups towards the transformations, both Wittig olefination and HWE reactions are a mainstay in the arsenal of organic synthesis. Here, an overview is given on Wittig-and Horner-Wadsworth-Emmons (HWE) reactions run in combination with other transformations in one-pot procedures. The focus lies on one-pot oxidation Wittig/HWE protocols, Wittig/HWE olefinations run in concert with metal catalyzed cross-coupling reactions, Domino Wittig/HWE-cycloaddition and Wittig-Michael transformations.

show abstract

Section: Resultsmentioning

confidence: 99%

“…In their synthesis to C-glycoside amphiphiles, Ranoux et al followed a similar strategy, reacting non-protected sugars with HWE reagents in aqueous or solventless conditions, leading to C-glucosides 117 and 121 (Scheme 31) [155].…”

Section: Scheme 29 Wittig Reaction-cyanosilylationmentioning

confidence: 99%

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Merza¹,

Taha²,

Thiemann³

2018

Alkenes

View full text Add to dashboard Cite

show abstract

“…In our previous study we reinvestigated the HWE/Michael addition combination by enlarging the scope of this powerful sequence to aqueous and solvent free conditions and from native sugars [10]. We demonstrated that C-glycoside amphiphiles are accessible from this methodology when Scheme 1 HWE/Michael addition sequence for the preparation of C-pyranosides and/or C-furanosides.…”

Section: Introductionmentioning

confidence: 95%

“…Solvent-free HWE reaction followed by a simple aqueous basic treatment yielded pure -C-glycosidic ketones with various alkyl chain lengths. In particular, C-glycosides derived from lactose, D-glucose and D-galactose possessing a short (C 7 ) alkyl chain 4-6 ( Figure 1) were obtained in moderate to good yields and high  selectivity [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents

2010

Self Cite

View full text Add to dashboard Cite

International audienceThis work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di- or mono-saccharides. A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties. The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short (C7) alkyl chain are also described and compared with those of commercial O-glucoside references

show abstract

“…Examples for Wittig reactions with unprotected carbohydrates are summarized in reference [13][14][15][16][17][18][19][20][21][22][23], for reviews in this field see [24][25][26], whereas examples for Horner olefination (even in aqueous reaction medium) will be found in reference [27,28]. The reactions were carried out mostly at higher temperature.…”

mentioning

confidence: 99%

Organocatalyzed Cascade Reaction in Carbohydrate Chemistry

Mahrwald

2015

SpringerBriefs in Molecular Science

View full text Add to dashboard Cite

The extensive and extremely strong development of organocatalysis over the last years provided versatile methodologies for convenient utilization of the carbonyl function of unprotected carbohydrates in C-C-bond formation processes. These biomimetic amine-activated mechanisms enable multiple cascade-protocols for the synthesis of a large scope of carbohydrate derived compound classes. Several, only slightly different protocols have been developed for the application of 1.3-dicarbonyls in stereoselective chain-elongation of unprotected carbohydrates and the synthesis of highly functionalized C-glycosides of defined configuration. Furthermore, the latter class of compounds can also be accessed by the use of methyl ketones. So a high substrate scope is available for the installation of desired functionalities in C-glycosides. By a one-pot, operationally simple cascade reaction of isocyanides with unprotected aldoses and amino acids an access to a broad range of defined glycosylated pseudopeptides is given. The elaborated organocatalyzed cascade-reactions provide defined access to highly functionalized carbohydrate derivatives. Depending on the reaction conditions different origin to control the installation of configuration during the bond-formation process were observed. The demonstrated organocatalyzed cascade sequences indicate the great potential of unprotected carbohydrates in the synthesis of highly functionalized bio-mimetic structure motifs by operationally simple, one-pot protocols.Due to the great biological importance of carbon chain elongated carbohydrates, the synthesis of this structural diverse compound class has attracted high synthetic interest from the scientific community. Among the elongated carbohydrates, C-Glycosides have gained considerable importance over the last few decades, since they are configuratively stable under enzymatic conditions and less prone to cleavage at the anomeric carbon. As such they are appealing substrates for chemical biology and medicinal chemistry.

show abstract

Horner–Wadsworth–Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One‐Step Access to C‐Glycoside Amphiphiles

Cited by 41 publications

References 11 publications

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents

Organocatalyzed Cascade Reaction in Carbohydrate Chemistry

Contact Info

Product

Resources

About