- Nickel-Catalyzed system for the cross-coupling of alkenyl methyl ethers with grignard reagents under mild conditions
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A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.
- Hostier, Thomas,Neouchy, Zeina,Ferey, Vincent,Gomez Pardo, Domingo,Cossy, Janine
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supporting information
p. 1815 - 1818
(2018/04/14)
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- Synthesis of Substrates for Aldolase-Catalysed Reactions: A Comparison of Methods for the Synthesis of Substituted Phenylacetaldehydes
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Methods for the synthesis of phenylacetaldehydes (oxidation, one-carbon chain extension) were compared by using the synthesis of 4-methoxyphenylacetaldehyde as a model example. Oxidations of 4-methoxyphenylethanol with activated DMSO (Swern oxidation) or manganese dioxide gave unsatisfactory results; whereas oxidation with 2-iodoxybenzoic acid (IBX) produced 4-methoxyphenylacetaldehyde in reasonable (75%) yield. However, Wittig-type one-carbon chain extension with methoxymethylene-triphenylphosphine followed by hydrolysis gave an excellent (81% overall) yield of 4-methoxyphenylacetaldehyde from 4-methoxybenzaldehyde (a cheap starting material). This approach was subsequently used to synthesise a set of 10 substituted phenylacetaldehydes in good to excellent yields.
- Al-Smadi, Derar,Enugala, Thilak Reddy,Norberg, Thomas,Kihlberg, Jan,Widersten, Mikael
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supporting information
p. 1187 - 1190
(2018/03/26)
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- Asymmetric synthesis of O-methylneferine
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Diastereoselective Pictet-Spengler reaction of 2-arylethylamine bearing an N-(R)-1-(1-naphthyl)ethylcarbamoyl group with arylacetaldehyde gave 1-benzyltetrahydroisoquinoline in good yield with moderate diastereoselectivity. The reaction was applied to asymmetric synthesis of O-methyl derivative of neferine, an alkaloid of the lotus embryo, Nelumbo nucifera Gaertner.
- Nishimura, Katsumi,Horii, Shinji,Tanahashi, Takao
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p. 865 - 876
(2019/04/26)
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- Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity
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An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(5-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR
- Lam, Raphael H.,Walker, D. Barney,Tucker, Matthew H.,Gatus, Mark R. D.,Bhadbhade, Mohan,Messerle, Barbara A.
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supporting information
p. 4312 - 4317
(2015/09/22)
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- Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: An electron transfer pathway?
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Potassium alkoxides undergo anti-Markovnikov addition to aryl-substituted alkynes with Z selectivity in DMF as the solvent. The yields and efficiency of the reaction was also found to be enhanced by the addition of a secondary amine ligand such as N,N′-di
- Cuthbertson, James,Wilden, Jonathan D.
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p. 4385 - 4392
(2015/06/08)
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- Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes
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We report here the first transition-metal-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes to give enol ethers in high yields without using bases. Arylacetylenes as well as alkenyl- and alkylacetylenes were coupled with aliphatic alcohols, and the products were obtained with high Z selectivity in most cases. Effective catalysts were 8-quinolinolato rhodium complexes, which are structurally simple but have been relatively unexplored as catalysts.
- Kondo, Masataka,Kochi, Takuya,Kakiuchi, Fumitoshi
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supporting information; experimental part
p. 32 - 34
(2011/03/16)
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- Practical regioselective method for (E)-enol ehter
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A new practical and highly regioselective synthetic method for (E)-enol ether is reported. (E)-enol ethers (E:Z = 93:7-99:1) were prepared from the corresponding enol acetates (E:Z?3:1) in two steps by bromination and anti- elimination of α-bromodialkylac
- Park, Hyeung-Geun,Kim, Dong-Hwa,You, Misuk,Park, Mi-Kyoung,Jew, Sang-Sup
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p. 4579 - 4582
(2007/10/03)
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- A unified strategy for the synthesis of phenanthroizidine alkaloids: Preparation of sterically congested pyridines
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Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe
- Ciufolini, Marco A.,Roschangar, Frank
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p. 12082 - 12089
(2007/10/03)
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- Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
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Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity.Di- and trisubstituted olefin derivatives are available through this procedure.Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization.The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring.This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.
- Alcaide, Benito,Perez-Castells, Javier,Polanco, Concepcion,Sierra, Miguel A.
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p. 6012 - 6016
(2007/10/03)
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- A Novel Fragmentation of the β-Lactam Ring: Stereoselective Entry to Vinyl Ethers by Reaction of N-(Arylidene(or alkylidene)amino-2-azetidinones with Ozone
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The title compounds undergo a novel 2-azetidinone ring fragmentation by reaction with ozone followed by NaBH4 workup to stereoselectively yield vinyl ethers via intermediate N-nitroso-β-lactams.
- Alcaide, Benito,Miranda, Miguel,Perez-Castells, Javier,Sierra, Miguel A.
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p. 297 - 298
(2007/10/02)
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- Photolysis of Vinyl Halides. Preferential Formation of Vinyl Cations by Copper(II) Salts
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Photolysis of vinyl halides in the presence of copper(II) salts in a significant suppression of product formation derived from vinyl radicals.Photolysis of 1,1-diaryl-2-bromopropenes in the presence of copper(II) salts yielded no 1,1-diaryl-2-propenes.Photolysis of other vinyl halides, i.e., 1,1-diaryl-2-iodopropenes, 1,1-diaryl-2-bromoethylenes, and 1-bromo-2-(p-methoxyphenyl)ethylene, also led to a large decrease in the yields of the reduced olefins derived from the vinyl radicals.Copper(II) triflate was found to be more effective for the oxidation of vinyl radicals than copper(II) acetate.These reactions are explained by the intervention of vinylcopper intermediates and the formation of vinyl cations.
- Kitamura, Tsugio,Kobayashi, Shinjiro,Taniguchi, Hiroshi
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p. 2641 - 2645
(2007/10/02)
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