Synthesis of <i>trans</i>‐Configured Enol Ethers by a Sequence of <i>syn</i>‐Selective Glycolate Aldol Addition, Hydrolysis, and Grob Fragmentation

Engesser, Tobias A.; Brückner, Reinhard

doi:10.1002/ejoc.201701197

Cited by 3 publications

(2 citation statements)

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“…Despite extensive applications of enol ethers, still there is lack of general and direct method for their synthesis. Metal-catalyzed couplings are the most common available method [ 50 – 54 ], along with some other indirect methodologies [ 55 – 62 ]. Direct synthesis of enol ethers by a Wittig reaction with alkoxymethylphosphonium salt is though an evident concept but no systematic study is found in literature.…”

Section: Resultsmentioning

confidence: 99%

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Gondal

Cheema

Zaidi

et al. 2018

Chemistry Central Journal

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An efficient one pot method for the synthesis of α-alkoxymethylphosphonium iodides is developed by using PPh3/I2 combination at room temperature. Reaction conditions are found general to synthesize wide range of structurally variant alkoxymethylphosphonium iodides in high yield (70–91%). These new functionalized phosphonium salts are further used in stereoselective synthesis of vinyl ethers as well as in carbon homologation of aldehydes.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0421-6) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Gondal

Cheema

Zaidi

et al. 2018

Chemistry Central Journal

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“…T. Engesser et al 94,102,126 In all substrates, O α was protected (alkyl, aryl, MOM) but never silylated. Many aldehydes have been engaged, also in combinatorial synthesis.…”

Section: Scheme 20 Syn-selective Aldol Addition Of the Et 2 B Enolatementioning

confidence: 99%

Stereoselective Aldol Additions of Glycolic Acid and Its Derivatives

Engesser¹,

Brückner²

2019

Synthesis

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This review gives a comprehensive overview of aldol additions of glycolic acid derivatives to achiral aldehydes and acetals affording α,β-dihydroxycarboxylic acids or derivatives thereof. The focus is on simple diastereoselectivity. A selection of related aldol additions is also presented: aldol additions of glycolic acid derivatives to ketones with two different substituents and aldol additions of α-substituted glycolic acid derivatives.1 Introduction1.1 Organization of this Review1.2 Outside the Scope of this Review: Aldol Additions Giving α,β-Dihydroxyaldehydes and α,β-Dihydroxyketones Diastereoselectively1.3 Non-Aldol Routes to Diastereomerically Pure α,β-Dihydroxycarboxylic Acid Derivatives2 Aldol Additions of Glycolic Acid (Derivative) Enolates to Aldehydes2.1 Aldol Additions of Glycolate Enolates (‘Glycolic Acid Dianions’)2.2 Aldol Additions of Glycolic Ester Enolates2.3 Aldol Additions of Glycolic Thioester Enolates2.4 Aldol Additions of Glycolimide Enolates2.5 Aldol Additions of Glycolamide Enolates2.6 Mukaiyama Aldol Additions of Silyl Ketene Acetals of Glycolic Esters and Thioesters2.7 Aldol Additions of Glycoloyl Chlorides via Acyl Ammonium Enolates3 Aldol-Providing Substitutions of Glycolimide Enolates in Acetals4 Additions Related to Aldol Additions of Glycolic Acid Derivative Enolates to Aldehydes4.1 Selected Simply Diastereoselective Aldol Additions of Enolates of Glycolic Acid Derivatives to Ketones with Two Different Substituents4.2 Simply Diastereoselective Aldol Additions of Enolates of Glycolic Acid Derivatives with a Methyl Substituent at C-α (Lactic Acid Derivatives)5 Conclusion

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Titanium-catalyzed highly stereoselective anti-Markovnikov intermolecular hydroalkoxylation of alkynes to prepare Z-enol ethers

Wang,

Ma,

Mao

et al. 2023

Org. Biomol. Chem.

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Synthesis of trans‐Configured Enol Ethers by a Sequence of syn‐Selective Glycolate Aldol Addition, Hydrolysis, and Grob Fragmentation

Cited by 3 publications

References 60 publications

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Stereoselective Aldol Additions of Glycolic Acid and Its Derivatives

Titanium-catalyzed highly stereoselective anti-Markovnikov intermolecular hydroalkoxylation of alkynes to prepare Z-enol ethers

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