Reaction Of Sulfur Ylides Research Articles

Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: scope, selectivity, and applications in synthesis.

The reaction of sulfur ylides with carbonyl compounds to give epoxides is an important synthetic method. This Account charts the recent advances in rendering this process both asymmetric and catalytic. Two catalytic methods have been developed: the first involving the reaction of a sulfide with an alkyl halide in the presence of a base and aldehyde and the second involving the reaction of a sulfide with a diazo compound or diazo precursor in the presence of a metal catalyst and aldehyde. These catalytic methods coupled with suitable chiral sulfides provide a new catalytic asymmetric epoxidation process for the preparation of epoxides. The scope of the two catalytic processes is discussed together with the factors that influence both relative and absolute stereochemistry. The application of these methods in target-orientated synthesis is also reviewed.

A New Reaction of Sulfur Ylides. Imination of Dimethylsulfonium Ketoylides with Tosyl Isocyanate.

AbstractFor Abstract see ChemInform Abstract in Full Text.

A convergent synthetic approach to the nucleoside-type liposidomycin antibiotics.

[reaction: see text] A synthetic approach toward the liposidomycins, a family of complex nucleoside-type antibiotics, is reported based on the synthesis of epoxy-amides derived from the reaction of sulfur ylides with the uridyl aldehyde derivative 6. To this end, the epoxy-amide derivative of indoline 14 was stereoselectively prepared and, after treatment with DDQ, transformed into the corresponding N-indole epoxyamide 15. The indole 15 provides ready access to a variety of structures related to the diazepanone core present in the liposidomycins by reaction with a variety of amines.

A new reaction of sulfur ylides. Imination of dimethylsulfonium ketoylides with tosyl isocyanate

A new reaction of sulfur ylides. Imination of dimethylsulfonium ketoylides with tosyl isocyanate

ChemInform Abstract: Microwave‐Assisted Synthesis of Substituted Cyclopropyl Ferrocenyl Ketones by a Sulfur Ylide Reaction under Solid‐State Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds

The combination of the Sharpless asymmetric epoxidation reaction with a sulfur ylide mediated synthesis of allylic alcohols from epoxides provides a powerful iterative process for the production of polyoxygenated compounds. The alkene installed in the sulfur ylide reaction has also been used in a number of ring closing metathesis reactions to produce highly oxygenated cyclic compounds.

ChemInform Abstract: Stereoselective Synthesis of Precursors of the Macrolide Antibiotics via Reactions of Sulfur Ylides with Chiral Aldehydes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes

Reactions of stabilized sulfur ylides with chiral aldehydes provided epoxides with high stereoselectivity. The opening of the resulting epoxides with lithium dimethyl cuprate gave 2-methyl-3-hydroxy amides which represent potentially useful building blocks for the synthesis of macrolide natural products. These amides were transformed into chiral aldehydes, with a methyl group in the α-position, and were reacted, in a iterative process, with a sulfur ylide reagent to give, in high yield and stereoselectivity, the epoxides with the stereochemistry according to Felkin-Ahn control. Finally, opening of the epoxide with the Gilman reagent provided a compound with four stereocenters occurring in the macrolide-type of natural products.

Catalytic sulfur ylide reactions: Use of diazoacetamides for the diastereoselective synthesis of glycidic amides

Diazoacetamides react with aldehydes in the presence of catalytic quantities of Cu(acac) 2 (5 mol%) and tetrahydrothiophene (20 mol%) to give glycidic amides in good yields and high diastereoselectivity.

ChemInform Abstract: Reactions of Sulfur Ylides with α,β‐Unsaturated Thioamides: Synthesis of Dihydrothiophenes and Cyclopropanes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reactions of sulfur ylides with α,β-unsaturated thioamides: Synthesis of dihydrothiophenes and cyclopropanes

The reactions of stabilized sulfonium ylides with arylmethylenecyanothioacetamides proceed stereoselectively to yield 2-amino-4,5-dihydrothiophenes and cyclopropane-thiocarboxamides. The structures of the latter compounds were confirmed by X-ray diffraction analysis.

ChemInform Abstract: Novel Synthesis of Vinyl Cyclopropane Carboxylic Acids: Application to the Synthesis of (d,l)‐ and (d)‐cis‐Chrysanthemic Acid.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Novel synthesis of vinyl cyclopropane carboxylic acids: Application to the synthesis of ( d, l)- and ( d)- cis-chrysanthemic acid

Reaction of sulfur ylides with suitably 4-functionalized-5,5-dimethyl-2-cyclopentenones allows an efficient entry to the bicyclo[3.1.0]hexan-2-one skeleton which proved to be a valuable precursor of vinyl cyclopropane carboxylic acids. Application to the synthesis of ( d, l)- and ( d)-( cis)-chrysanthemic acid is described.

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Pentacoordinate oxaphosphetanes, oxasiletanides, oxagermetanides, oxastannetanides, and tetracoordinate oxaboretanides were successfully synthesized as stable intermediates of the Wittig reaction, the Peterson reaction, Peterson-type reactions, and boron-Wittig reaction, respctively Tetracoordinate and pentacoordinate oxathietanes, tetracoordinate oxaselenetanes and pentacoordinate azaphosphetidines were also synthesized as their sulfur and selenium-analogs, and aza-analog of oxaphosphetanes. The X-ray crystallographic analyses of Si, Ge, P, S, and Se compounds indicated that they have a distorted trigonal bipyramidal structure with two apical oxygen atoms, but those of B, Sn, and another type of Ge compounds demonstrated that they have a very distorted tetrahedral boron, a nearly square pyramidal tin, and a tetrahedral germanium strongly interacting with an oxido anion, respectively. Expectedly, on heating all compounds containing group 13, 14, and 15 elements underwent the Wittig-type reaction to give the corresponding olefins. Although the thermolysis of oxachalcogenetanes with a tetracoordinate and pentacoordinate S and Se centers gave no olefin, it was suggested that the former compounds are intermediates of the Corey-Chaykovsky reaction of sulfur ylides.

ChemInform Abstract: Chromium Carbenes as Substrates in Cyclopropanation Reactions: 1,4‐ vs 1,2‐Addition in the Reaction of Sulfur Ylides and α,β‐ Unsaturated Alkoxychromium(0) Carbenes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Chromium Carbenes as Substrates in Cyclopropanation Reactions: 1,4- vs 1,2-Addition in the Reaction of Sulfur Ylides and .alpha.,.beta.-Unsaturated Alkoxychromium(0) Carbenes

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChromium Carbenes as Substrates in Cyclopropanation Reactions: 1,4- vs 1,2-Addition in the Reaction of Sulfur Ylides and .alpha.,.beta.-Unsaturated Alkoxychromium(0) CarbenesBenito Alcaide, Luis Casarrubios, Gema Dominguez, Miguel A. Sierra, and Jesus Jimenez-BarberoCite this: Organometallics 1994, 13, 8, 2934–2936Publication Date (Print):August 1, 1994Publication History Published online1 May 2002Published inissue 1 August 1994https://doi.org/10.1021/om00020a007RIGHTS & PERMISSIONSArticle Views110Altmetric-Citations10LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (394 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Synthesis of α- and β- D,L- ribo-carbahex-2-ulofuranose

Both α- and β-D,L-ribo-carbahex-2-ulofuranose have been synthesized in racemic form starting from norbornen-2-one. In the course of the synthesis the reaction of sulfur ylides with α-alkoxyketones took an unexpected stereochemical pathway.

Arsirane synthesis by reaction of sulfur ylides with diazaarsoles

N-unsubstituted diazaarsoles 4 undergo an N alkylation by reaction with sulfur ylides. N-substituted diazaarsoles 5 and 9 react with dimethylsulfoxonium ylide to give stable bicyclic arsiranes 11 and 12 .

ChemInform Abstract: Reaction of Sulfur Ylides with Elemental Sulfur and Selenium. Aspects and Mechanistic Considerations.

AbstractReaction of the sulfonium ylides (I) with sulfur or selenium produces the olefins (II) via the intermediate thio‐ or selenocarbonyl compounds.

Reaction of sulfur ylides with elemental sulfur and selenium. Aspects and mechanistic considerations

AbstractThe reaction of sulfur ylides with elemental sulfur or selenium initially affords thio‐ or seleno‐carbonyl compounds, which then react with starting ylides to give episulfides or episelenides from which the heteroatom (sulfur or selenium) is extruded to give olefins as the final product. In the case of carbonyl‐stabilized ylides, the resulting thio‐ or seleno‐carbonyl compounds react with starting ylides to afford 1,3‐oxathioles or 1,3‐oxaselenoles as previously reported. Supporting evidence for the intermediacy of thio(seleno)‐carbonyl compounds and episulfides (episelenides) is presented.