Reaction of silyl enol ethers with β-halogenoalkyl aryl sulfides - a method of β-arylthioalkylation of carbonyl compounds

Ibragimov, M. A.; Smit, W. A.

doi:10.1016/s0040-4039(00)81577-4

Cited by 27 publications

(2 citation statements)

References 6 publications

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“…Hydrogenolysis gives overall the product 697 of addition by a hydroxy and a benzyl group (Scheme 171). 415 Episulfonium ions 698 and 699 are attacked by silyl enol ethers stereospecifically with inversion of configuration at the electrophilic carbon (Scheme 172), 416 even when that carbon is tertiary, 417 and episelenenium ions are similarly opened by silyl enol ethers in a reaction exactly parallel to that illustrated in Scheme 172. 418 The reaction between the R-acetoxy N,N-dimethylhydrazone 700 and silyl enol ethers 537 probably takes place by way of the cation 701, and gives the N,N-dimethylhydrazone 702 of a 1,4-dicarbonyl compound.…”

Section: E Intermolecular Attack By Other Electrophilesmentioning

confidence: 98%

“…Episulfonium ions 698 and 699 are attacked by silyl enol ethers stereospecifically with inversion of configuration at the electrophilic carbon (Scheme ), even when that carbon is tertiary, and episelenenium ions are similarly opened by silyl enol ethers in a reaction exactly parallel to that illustrated in Scheme 172 …”

Section: E Intermolecular Attack By Other Electrophilesmentioning

confidence: 98%

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Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

1997

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Section: E Intermolecular Attack By Other Electrophilesmentioning

confidence: 98%

Section: E Intermolecular Attack By Other Electrophilesmentioning

confidence: 98%

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

1997

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The Asymmetric Vinylogous Mukaiyama Aldol Reaction

Cordes

Kalesse

2019

Organic Reactions

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The vinylogous Mukaiyama aldol (VMA) reaction allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di‐ and tri‐substituted double bonds in a single operation. In this chapter, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed.

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Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Free Radical Alkylation Direct Alkylation or Acylation / Organocatalysis Direct Enol or Enolate Alkylation and Acylation Enol Ethers Enol Esters Enol Boranes Enol Alanes Enol Gallium Compounds Enol Silanes Enol Stannanes and Related Compounds Enol Phosphorus Compounds Enol Triflates Enamines Nitroalkenes Imines Hydrazones Oxime Ethers Oximes Blocking Groups Alkylation and Acylation of Carbonyl Dianions Alkylation and Acylation of β‐Ketoaldehydes Alkylation and Acylation of β ‐Diketones Alkylation and Acylation of β‐Polyketones Synthesis of β‐Keto Acids, Esters, Amides, Imides, and Nitriles and Decarboxylation Alkylation and Acylation of Enones

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Reaction of silyl enol ethers with β-halogenoalkyl aryl sulfides - a method of β-arylthioalkylation of carbonyl compounds

Cited by 27 publications

References 6 publications

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

The Asymmetric Vinylogous Mukaiyama Aldol Reaction

Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives

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