64304-83-2Relevant academic research and scientific papers
Nickel-Catalyzed system for the cross-coupling of alkenyl methyl ethers with grignard reagents under mild conditions
Hostier, Thomas,Neouchy, Zeina,Ferey, Vincent,Gomez Pardo, Domingo,Cossy, Janine
supporting information, p. 1815 - 1818 (2018/04/14)
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.
Synthesis of Substrates for Aldolase-Catalysed Reactions: A Comparison of Methods for the Synthesis of Substituted Phenylacetaldehydes
Al-Smadi, Derar,Enugala, Thilak Reddy,Norberg, Thomas,Kihlberg, Jan,Widersten, Mikael
supporting information, p. 1187 - 1190 (2018/03/26)
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.
Asymmetric synthesis of O-methylneferine
Nishimura, Katsumi,Horii, Shinji,Tanahashi, Takao
, p. 865 - 876 (2019/04/26)
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.
Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity
Lam, Raphael H.,Walker, D. Barney,Tucker, Matthew H.,Gatus, Mark R. D.,Bhadbhade, Mohan,Messerle, Barbara A.
supporting information, p. 4312 - 4317 (2015/09/22)
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
Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: An electron transfer pathway?
Cuthbertson, James,Wilden, Jonathan D.
, p. 4385 - 4392 (2015/06/08)
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
Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes
Kondo, Masataka,Kochi, Takuya,Kakiuchi, Fumitoshi
supporting information; experimental part, p. 32 - 34 (2011/03/16)
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.
Practical regioselective method for (E)-enol ehter
Park, Hyeung-Geun,Kim, Dong-Hwa,You, Misuk,Park, Mi-Kyoung,Jew, Sang-Sup
, p. 4579 - 4582 (2007/10/03)
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
A unified strategy for the synthesis of phenanthroizidine alkaloids: Preparation of sterically congested pyridines
Ciufolini, Marco A.,Roschangar, Frank
, p. 12082 - 12089 (2007/10/03)
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
Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
Alcaide, Benito,Perez-Castells, Javier,Polanco, Concepcion,Sierra, Miguel A.
, p. 6012 - 6016 (2007/10/03)
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.
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
Alcaide, Benito,Miranda, Miguel,Perez-Castells, Javier,Sierra, Miguel A.
, p. 297 - 298 (2007/10/02)
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.
