64304-84-3

Upstream product

• 145654-48-4 (3S,4R)-3-Methoxy-4-(4-methoxy-phenyl)-1-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-azetidin-2-one 
• 67-56-1 methanol 
• 768-60-5 4-methoxyphenylacetylen 
• 865-33-8 potassium methanolate 
• 124-41-4 sodium methylate 
• 864816-16-0 2-methoxy-3-(4-methoxyphenyl)-2-propenoic acid 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Nickel-Catalyzed system for the cross-coupling of alkenyl methyl ethers with grignard reagents under mild conditions

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

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

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.

Pd-Catalyzed Regioselective Decarboxylative/C-H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers

A direct introduction of vinyl ethers into C-H bond of heterocycles is reported. For this purpose, decarboxylative direct C-H cross-coupling of 1,3-diazoles with α-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various α-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.

Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: An electron transfer pathway?

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

Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity

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

Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes

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.

Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone

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.