Journal ArticleDOI
Palladium(II)-catalyzed isomerization-Claisen rearrangement of 2-alkoxy diallyl ethers
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TLDR
In this article, the authors show that in the presence of PdCl2 as a catalysts, Diallyl ethers bearing an enol ether react to give α-allyl α-alkoxy ketones by selective isomerization via 1,2-H migration at the more substituted allyl group, followed by Claisen rearrangement.About:
This article is published in Tetrahedron.The article was published on 2004-10-18. It has received 31 citations till now. The article focuses on the topics: Carroll rearrangement & Claisen rearrangement.read more
Citations
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Gold-Catalyzed Organic Reactions
TL;DR: Important vinylgold intermediates, the transmetalation from gold to other transition metals, the development of new ligands for gold catalysis, and significant contributions from computational chemistry are other crucial points for the field highlighted here.
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Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.
TL;DR: The proposed involvement of cyclopropyl metal carbenes of type 4 in the electrophilic activation of enynes by transition metals was first substantiated in reactions catalyzed by Pd(II), in which the initially formed cycloprostyl palladiumCarbenes undergo [4 + 2] cycloaddition with the double bond of the conjugate enyne.
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Catalysis of the Claisen rearrangement
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Missing cyclization pathways and new rearrangements unveiled in the gold(I) and platinum(II)-catalyzed cyclization of 1,6-enynes
TL;DR: In this paper, a cyclopropyl metal carbenes formed in the 6-endo-dig cyclization may evolve to form seven-membered ring intermediates using highly electrophilic platinum(II) and gold(I) complexes.
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Transition metal-catalyzed alkene isomerization as an enabling technology in tandem, sequential and domino processes.
TL;DR: This Review covers seminal and recent examples of tandem, sequential and domino processes, which incorporate the most attractive features of olefin isomerization.
References
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Journal ArticleDOI
Cationic Gold(I) Complexes: Highly Alkynophilic Catalysts for the exo‐ and endo‐Cyclization of Enynes
Cristina Nieto-Oberhuber,M. Paz Muñoz,Elena Buñuel,Cristina Nevado,Diego J. Cardenas,Antonio M. Echavarren +5 more
TL;DR: The first examples of endocyclic skeletal rearrangements under mild conditions have been observed with alkynophilic cationic gold(I) complexes.
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Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions.
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Platinum-Catalyzed Cycloisomerization Reactions of Enynes
TL;DR: Strong experimental support for the proposed mechanism comes from deuterium-labeling studies, a careful analysis of the product distribution pattern, and the fact that in some cases PtCl(2) can be replaced by simple Lewis or Brønsted acids as the catalysts.