Preparation of siloxacyclopentene containing 1,3-dienes and their Diels–Alder reactions

Pidaparthi, Ramakrishna R.; Welker, Mark E.

doi:10.1016/j.tetlet.2007.08.133

Cited by 19 publications

(8 citation statements)

References 14 publications

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“…This union of a carbonyl and an alkynylsilane is postulated to occur through the hydrosilylation of an oxasilicate intermediate 101 which arises from silylative alkyne addition to the carbonyl. This pathway appears to be validated by the results of Roush 123 and Welker124 who obtained the same oxasilacycles from the treatment of propargylic alkoxysilanes with catalytic butoxide (Scheme 40, equation 2). Enynes such as 102 also react in good yields, giving endocyclic silyldiene products 103, in this instance also tolerating bulkier alkyl substituents on the silicon (Scheme 40, equation 3).…”

supporting

confidence: 59%

Synthesis of Vinylsilanes

Lim¹,

Anderson²

2012

Synthesis

116

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supporting

confidence: 59%

Synthesis of Vinylsilanes

Lim¹,

Anderson²

2012

Synthesis

116

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“…3 Krische and co-workers have also reported a ruthenium catalyzed hydrohydroxyalkylation of silyl substituted 1,3 butadienes in 2011 as well. 4 We reported our initial studies in 2007 5,6 and 2009 7 on the preparation and reaction chemistry of 2-trialkoxysilyl-1,3-butadienes. In 2010 we reported a ruthenium catalyzed ene-yne metathesis route to silyl substituted 1,3 dienes which we subsequently used in thermal Diels-Alder reactions.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Ruthenium carbenes as catalysts in stereoselective ene–yne metathesis/Diels–Alder and ene–yne metathesis/Diels–Alder/cross coupling multicomponent reactions

Junker¹,

Welker²

2012

Tetrahedron

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Please cite this article as: Junker CS, Welker ME, Ruthenium Carbenes as Catalysts in stereoselective ene-yne Metathesis/Diels-Alder and ene-yne Metathesis/Diels-Alder/Cross coupling multicomponent reactions, Tetrahedron (2012Tetrahedron ( ), doi: 10.1016Tetrahedron ( /j.tet.2012 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractAn ene-yne cross metathesis of silyl substituted alkynes and alkenes followed by a Diels-Alder reaction of the metathesis product 2-silyl-1,3-dienes has been developed.The dienes thus prepared in situ were shown to participate in highly diastereoselective Diels-Alder reactions. In one case the silicon substituted Diels-Alder cycloadduct was subsequently used without isolation and purification in a Hiyama cross coupling reaction.The cross coupling reactions enable these silicon dienes to be used as synthons for a variety of other dienes.

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“…Initially, we prepared a number of transition metal-substituted dienes [1,2] for these studies but, more recently, we have been interested in the investigation of silicon- and boron-substituted dienes [3,4,5,6,7]. We have reported the preparation of 2-silicon-substituted 1,3-butadienes by a variety of synthetic routes and demonstrated that they could be used in sequential Diels-Alder/cross-coupling reactions [8,9,10,11,12,13]. Here we report the preparation of new 2-silicon-substituted 1,3-dienes containing silicon substituents known to promote transmetallation (hence, the ability to participate in cross-coupling reactions under very mild conditions) and their Diels-Alder/cross-coupling reactions.…”

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Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes

Choudhury

Welker

2015

Molecules

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2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio-and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.

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Preparation of siloxacyclopentene containing 1,3-dienes and their Diels–Alder reactions

Cited by 19 publications

References 14 publications

Synthesis of Vinylsilanes

Synthesis of Vinylsilanes

Ruthenium carbenes as catalysts in stereoselective ene–yne metathesis/Diels–Alder and ene–yne metathesis/Diels–Alder/cross coupling multicomponent reactions

Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes

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