Intramolecular Addition Of Allylsilanes Research Articles

Tetrabutylammonium Triphenyldifluorosilicate (TBAT) Initiated Intramolecular Addition of Allylsilanes to 2,3‐Dihydro‐4‐pyridones. A Novel Route for the Stereoselective Construction of Indolizidine Systems.

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Tetrabutylammonium triphenyldifluorosilicate (TBAT) initiated intramolecular addition of allylsilanes to 2,3-dihydro-4-pyridones. A novel route for the stereoselective construction of indolizidine systems

A general and preparatively simple access to multisubstituted indolizidines has been developed. The key step involves the fluoride ion induced intramolecular reaction of 2,3-dihydro-4-pyridones with allylsilane located in the side-chain.

About the Stereoelectronics of the Intramolecular Addition of Allylsilanes to Aldehydes

About the Stereoelectronics of the Intramolecular Addition of Allylsilanes to Aldehydes

About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes.

(Z)-omega-Trimethylsilyl-(omega-2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega-1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z)-omega-trimethylsilyl-(omega-2)-alkenals which, in the presence of trifluoroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylcyclohexanol (2), isopulegol (4), and bis(2-vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interference of a novel electrodynamic effect.

A β-lactone-based route to cyclopentanes via intramolecular allylsilane additions. An unexpected friedel-crafts alkylation

Lewis acid promoted intramolecular additions of allylsilanes to β-lactones proceed smoothly to give variously substituted cyclopentanes. A proposed transition state assembly for this reaction guided our efforts to improve the stereoselectivity. A novel Friedel-Crafts alkylation of β-lactones is also described.

Asymmetric Synthesis of Unsaturated Pipecolic Acid Derivatives

Two enantiopure pipecolic acid derivatives having an olefinic moiety were synthesized from an intramolecular addition of allyl silanes on an iminium double bond. The iminium moiety was generated via a reaction of chiral β-amino alcohols with glyoxal.

Cyclooctane or cyclohexane annulations based on intramolecular additions of allylsilanes to conjugated dienones

The scope and limitations of alkenyl dienone cyclizations for the formation of fused cyclooctane or cyclohexane systems are described

Intramolecular additions of allylsilanes to conjugated dienones. A direct stereoselective synthesis of (.+-.)-14-deoxyisoamijiol

A 16-step synthesis of (±)-14-deoxisoamijiol is reported featuring an intramolecular addition of an allylsilane to a conjugated dienone to construct stereospecifically the dolastane skeleton

Intramolecular additions of allylsilanes in triquinane synthesis. Studies directed toward the total synthesis of (±)-hirsutene

The straightforward construction of the cis , anti , cis -cyclopenta[ a ]pentalene skeleton characteristic of (±)-hirsutene was achieved via the intramolecular addition of two functionalized cyclopentane rings linked by a one-carbon tether.

Intramolecular additions of allylsilanes to conjugated dienones. The synthesis of three perforanes

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIntramolecular additions of allylsilanes to conjugated dienones. The synthesis of three perforanesGeorge Majetich, Jean Defauw, and Clay RingoldCite this: J. Org. Chem. 1988, 53, 1, 50–68Publication Date (Print):January 1, 1988Publication History Published online1 May 2002Published inissue 1 January 1988https://doi.org/10.1021/jo00236a013RIGHTS & PERMISSIONSArticle Views1108Altmetric-Citations66LEARN 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 (2 MB) Get e-Alerts Get e-Alerts

Chelation control in the intramolecular addition of allylsilanes to carbonyl electrophiles

Use of chelation control to direct the stereochemical outcome of intramolecular additions of allylsilanes to β-dicarbonyl substrates is described. Excellent diastereoselectivity is achieved by titanium tetrachloride promoted cyclization of a wide variety of β-dicarbonyl substrates, and these reactions also proceed in high yield. Cyclizations occur under mild conditions and are highly chemoselectivc, providing direct routes to highly functionalized five-, six- and seven-membered carbocycles.

Geometrical limitations in the intramolecular addition of unsymmetrical allylsilanes to enones

The geometrical constraints of the fluoride-initiated and Lewis acid-catalyzed intramolecular addition of allylsilanes to enone systems were shown to be governed by kinetic-ring-size preferences. Molecules containing adjacent quaternary carbon atoms can be prepared using this method.

Regioselectivity in intramolecular addition of allylsilanes to conjugated dienones

The intramolecular addition of allylsilanes to conjugated dienones shows a divergence of regioselectivity as a function of reagent and substrate structure. The creation of 5-5, 6-5, 5-7, and 6-7 bicyclic ring systems is reported.

Diastereoselectivity in intramolecular additions of allylsilanes to enones

The nature of the catalyst governs the stereochemical outcome in the formation of substituted hydrindanones and related species via intramolecular Sakurai condensations.