Journal ArticleDOI
The (4+3)-cycloaddition reaction: simple allylic cations as dienophiles
TLDR
The (4+3)-cycloaddition of allylic cations to dienes is a powerful method for the direct synthesis of seven-membered rings and applications to the total synthesis of natural products and their analogues.About:
This article is published in Chemical Communications.The article was published on 2010-11-23. It has received 243 citations till now. The article focuses on the topics: Allylic rearrangement & Total synthesis.read more
Citations
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Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems
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[5 + 2] Cycloaddition Reactions in Organic and Natural Product Synthesis
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Allenamides: A Powerful and Versatile Building Block in Organic Synthesis
TL;DR: While the chemistry of other heteroatom-substituted allenes is of high impact and value to organic synthesis, allenamines should prove to be more attractive for developing stereoselective methodologies as well as rapid assembly of structural complexity.
Journal ArticleDOI
The (4+3)-cycloaddition reaction: heteroatom-substituted allylic cations as dienophiles
TL;DR: The (4+3)-cycloaddition of allylic cations to dienes is a powerful method for the direct synthesis of seven-membered rings and applications to the total synthesis of natural products and their analogues.
Journal ArticleDOI
(4+3) cycloaddition reactions of nitrogen-stabilized oxyallyl cations.
Andrew G. Lohse,Richard P. Hsung +1 more
TL;DR: The following article will provide an overview of this concept utilizing nitrogen-stabilized oxyallyl cations in (4+3) cycloadditions.
References
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Journal ArticleDOI
Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction
Justin B. Siegel,Alexandre Zanghellini,Helena M. Lovick,Gert Kiss,Abigail R. Lambert,Jennifer L. St.Clair,Jasmine L. Gallaher,Donald Hilvert,Michael H. Gelb,Barry L. Stoddard,Kendall N. Houk,Forrest E. Michael,David Baker +12 more
TL;DR: The design of enzymes that catalyze the bimolecular Diels-Alder reaction, a carbon-carbon bond formation reaction that is central to organic synthesis but unknown in natural metabolism, is described.
Journal ArticleDOI
Proton-mediated chemistry and catalysis in a self-assembled supramolecular host.
TL;DR: This work provides rare examples of assembly-catalyzed reactions that proceed with substantial rate accelerations despite the absence of functional groups in the cavity and with mechanisms fully elucidated by quantitative kinetic studies.
Journal ArticleDOI
Application of Donor/Acceptor-Carbenoids to the Synthesis of Natural Products
TL;DR: This tutorial review will give an overview of the most versatile reactions of donor/acceptor carbenoids, an exciting class of intermediates capable of highly selective reactions, including cyclopropanation, [4 + 3] cycloaddition, and C-H functionalization methodologies.
Journal ArticleDOI
Steering the Surprisingly Modular π‐Acceptor Properties of N‐Heterocyclic Carbenes: Implications for Gold Catalysis
TL;DR: In this paper, the p acceptor properties of N-heterocyclic carbenes (NHCs) have been investigated and it was shown that the course of three mechanistically distinct gold-catalyzed processes can be determined solely by changing the pacceptor property of an ancillary NHC ligand.
Journal ArticleDOI
Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways
Isaac Alonso,Beatriz Trillo,Fernando López,Sergi Montserrat,Gregori Ujaque,Luis Castedo,Agustí Lledós,José L. Mascareñas +7 more
TL;DR: Experimental and theoretical data dismiss a cationic mechanism involving intermediate II and suggest that the formation of the [4C+2C] cycloadducts might arise from a 1,2-alkyl migration (ring contraction) in a cycloheptenyl Au-carbene intermediate (IV), itself arising from a [ 4C+3C] concerted cycloaddition of the allenediene.
Related Papers (5)
The (4+3)-cycloaddition reaction: heteroatom-substituted allylic cations as dienophiles
(4+3) cycloaddition reactions of nitrogen-stabilized oxyallyl cations.
Andrew G. Lohse,Richard P. Hsung +1 more