Journal ArticleDOI
[3+2] cycloadditions of allylsilanes - 4.
TLDR
In this article, the Lewis-acid-promoted reaction of allyltrimethylsilane with enones was shown to afford the 3-allyl ketone derivatives (Sakurai products) along with the trimethylsilylcyclopentanes ([3+2] cycloaddition products).About:
This article is published in Tetrahedron.The article was published on 1993-01-01. It has received 29 citations till now. The article focuses on the topics: Cycloaddition & Enone.read more
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Phosphine-catalyzed one-pot synthesis of cyclopentenes from electron-deficient allene, malononitrile and aromatic aldehydes
Xiyan Lu,Zheng Lu,Xumu Zhang +2 more
TL;DR: In this article, a three component reaction of aryl aldehydes and malononitrile with ethyl 2,3-butadienoate catalyzed by triphenylphosphine has been developed.
Journal ArticleDOI
Cycloadditions of allylsilances. Part 10. Stereoselective Construction of Ring Systems by Cycloaddition Reactions of allyltriisopropylsilance
TL;DR: Allyltriisopropylsilane is a useful reagent for the stereoselective construction of various ring systems by Lewis acid promoted formal cycloaddition reactions as mentioned in this paper.
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Tritylallyldimethylsilane−TiCl4 Annulations to Electron Deficient Olefins. Diastereomerically Pure 3-Substituted and 3,4-Disubstituted Cyclopentanols
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Synthesis of spirocarbamate oxindoles via intramolecular trapping of a β-silyl carbocation by an N-Boc group.
TL;DR: Several transformations display the synthetic utility of the Lewis acid catalyzed additions of allylsilanes to N-Boc-iminooxindoles, including a reductive cyclization to access new silylated furoindoline derivatives.
Journal ArticleDOI
Highly Stereoselective Synthesis of Bicyclo[n.3.0]alkanes by Titanium Tetrachloride Promoted [3 + 2] Cycloaddition of Allylsilanes and 1-Acetylcycloalkenes†
Hans-Joachim Knölker,Norbert Foitzik,Helmut Goesmann,Regina Graf,Peter G. Jones,Günter Wanzl +5 more
TL;DR: In this paper, the Hosomi-Sakurai reaction was suppressed in favor of the [3 + 2] cycloaddition by a systematic variation of the substituents at the silicon atom.
References
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The interaction of silicon with positively charged carbon
TL;DR: Sommer et al. as mentioned in this paper showed that a silyl group beta to the leaving group enormously enhances the rate of solvolysis, and that a gamma silyal group also has an enhancing effect, but that an alpha sily l group actually decreases reactivity in comparison with hydrocarbon models.
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Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enones
Akira Hosomi,Hideki Sakurai +1 more
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