The Retro‐Claisen Rearrangement of 2‐Vinylcyclopropylcarbonyl Substrates and the Question of its Synthetic Potential
Sign Up to like & getrecommendations! Published in 2020 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.202000136
Abstract: The retro-Claisen [3,3]-sigmatropic rearrangement of ,-enoyl compounds allows to form a CO bond while breaking a CC bond in a concerted process. It is rarely observed with acyclic substrates. However, when the alkene and carbonyl… read more here.
Keywords: rearrangement; retro claisen; claisen rearrangement; rearrangement vinylcyclopropylcarbonyl ... See more keywords
Stereocontrolled asymmetric synthesis of mollebenzylanols A and B using Claisen rearrangements
Sign Up to like & getrecommendations! Published in 2021 at "Tetrahedron"
DOI: 10.1016/j.tet.2021.131958
Abstract: Abstract Mollebenzylanol A, isolated in 2018, is a tyrosine phosphatase 1B inhibitor having a highly oxygenated structure, whereas mollebenzylanol B is its C15-epimer. Enantioselective total syntheses of mollebenzylanols A and B were accomplished in 13… read more here.
Keywords: stereocontrolled asymmetric; asymmetric synthesis; synthesis mollebenzylanols; mollebenzylanols using ... See more keywords
Revisiting Aromatic Claisen Rearrangement Using Unstable Aryl Sulfonium/Iodonium Species: The Strategy of Breaking Up the Whole into Parts.
Sign Up to like & getrecommendations! Published in 2022 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.2c00263
Abstract: ConspectusSince Ludwig Claisen's discovery of the sigmatropic rearrangement of allyl aryl ethers in 1912, aromatic Claisen rearrangement has continuously attracted the attention of both experimental and theoretical chemists. Over more than a century of growth,… read more here.
Keywords: aromatic claisen; claisen rearrangement; aryl; sulfonium ... See more keywords
A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c00763
Abstract: Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This… read more here.
Keywords: claisen rearrangement; synthetic strategy; cycloetherification; eight membered ... See more keywords
Synthesis of Benzofuran Derivates via a Gold-Catalyzed Claisen Rearrangement Cascade.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02388
Abstract: A novel method toward a facile synthesis of diverse benzofuran derivates from easily obtained quinols and alkynyl esters has been reported. A gold-catalyzed intermolecular alkoxylation/Claisen rearrangement/condensation cascade was involved. The introduction of difluorodiphenylsilane as a… read more here.
Keywords: gold catalyzed; benzofuran derivates; cascade; claisen rearrangement ... See more keywords
Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.8b03941
Abstract: An FeCl3-catalyzed allenic Claisen rearrangement/regio- and chemoselective aerobic dehydrogenative cyclization domino reaction is developed, providing a wide range of 2-aryl/alkyl, 3-(substituted-vinyl)naphtho[2,1- b]furans in high yields at 95-130 °C in an atom- and step-economic fashion. Mechanistic… read more here.
Keywords: rearrangement regio; claisen rearrangement; regio; aerobic dehydrogenative ... See more keywords
Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer
Sign Up to like & getrecommendations! Published in 2017 at "ACS Chemical Biology"
DOI: 10.1021/acschembio.6b00999
Abstract: The use of coumarin caged molecules has been well documented in numerous photocaging applications including for the spatiotemporal control of Cre-estrogen receptor (Cre-ERT2) recombinase activity. In this article, we report that 4-hydroxytamoxifen (4OHT) caged with… read more here.
Keywords: claisen rearrangement; coumarin; photo claisen; rearrangement coumarin ... See more keywords
Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.
Sign Up to like & getrecommendations! Published in 2020 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.0c11480
Abstract: A dual experimental/theoretical investigation of the Ireland-Claisen rearrangement of tetrasubstituted α-phthalimido ester enolates to afford α-tetrasubstituted, β-trisubstituted α-amino acids (generally >20:1 dr) is described. For trans allylic olefins, the Z- and E-enol ethers proceed through… read more here.
Keywords: claisen rearrangement; amino acids; ireland claisen; global diastereoconvergence ... See more keywords
Enantioselective aromatic Claisen rearrangement of allyl 2-naphthyl ethers catalyzed by π–Cu(ii) complexes
Sign Up to like & getrecommendations! Published in 2023 at "Chemical Science"
DOI: 10.1039/d2sc06771d
Abstract: The first catalytic enantioselective aromatic Claisen rearrangement of allyl 2-naphthyl ethers using 5–10 mol% of π–copper(ii) complexes is reported. A Cu(OTf)2 complex with an l-α-homoalanine amide ligand gave (S)-products in up to 92% ee. Conversely,… read more here.
Keywords: aromatic claisen; rearrangement allyl; claisen rearrangement; claisen ... See more keywords