39829-15-7

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 96-34-4 methyl chloroacetate 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 

Downstream Products

• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 79445-45-7 3-(3,4-Dimethoxyphenyl)pyridine 
• 54844-36-9 3-(3,4-dimethoxyphenyl)propane-1,2-diol 
• 54910-34-8 Pentamethyl-rosmarinat 
• 32255-79-1 2-hydroxy-3-(3,4-dimethoxyphenyl)propanoic acid 
• 130459-45-9 (-)-(2R,4R,5R)-2-(3,4-dimethoxybenzyl)-N-methyl-4-methyl-5-phenyloxazolidine 
• 130459-48-2 (-)-(2S,4S,5R)-2-(3,4-dimethoxybenzyl)-N-methyl-4-methyl-5-phenyloxazolidine 
• 130459-46-0 (2S,4R,5R)-2-(3,4-dimethoxybenzyl)-N-methyl-4-methyl-5-phenyloxazolidine 
• 130459-49-3 (2R,4S,5R)-2-(3,4-dimethoxybenzyl)-N-methyl-4-methyl-5-phenyloxazolidine 
• 125629-50-7 (+)-(S)-N-(3,5-dimethoxyphenethyl)halostachine 
• 130550-49-1 N-(3,5-dimethoxyphenethyl)halostachine 
• 130459-44-8 (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine 
• 130459-47-1 (-)-(1R,2S)-N-(3,4-dimethoxyphenethyl)ephedrine 
• 54814-41-4 (+/-)-(R)-methyl 3-(3,4-dimethoxyphenyl)-2-hydroxypropanoate 

Relevant academic research and scientific papers

Formal [3+2] cycloaddition reactions of electron-rich aryl epoxides with alkenes under Lewis acid catalysis affording tetrasubstituted tetrahydrofurans

We report on the regio- and stereoselective synthesis of tetrahydrofurans by reaction between epoxides and alkenes in the presence of a Lewis acid. This is an unprecedented formal [3+2] cycloaddition reaction between an epoxide and an alkene. The chemical reaction represents a very concise synthesis of tetrahydrofurans from accessible starting compounds.

Synthesis of 3-Arylpyridines via Palladium/Copper-Catalyzed Annulation of Allylamine/1,3-Propanediamine and Aldehydes

A novel and efficient method for the synthesis of 3-arylpyridines from allylamine/propanediamine and aldehydes by palladium/copper-catalyzed oxidative tandem cyclization has been developed. With this reaction, a series of desired 3-arylpyridines was synthesized in moderate yields via C-C/C-N bond formation and 6-endo/exo-trig cyclization.

An improved procedure for the epoxidation of methyl cinnamate derivatives and production of acid sensitive epoxides

By using a biphasic epoxidation system, unreactive methyl cinnamate derivatives were epoxidized at higher rates, and epoxides that decomposed in the presence of m-chlorobenzoic acid (mCBA) to diol ester opening products under standard conditions were obtained in fair to excellent yields.

Tricarbonylchromium(0) Promoted Stereoselective Cyclisations of the N-3,4-Dimethoxyphenethyl Derivatives of the 1-Phenyl Ethanolamines Halostachine, Ephedrine and Pseudoephedrine to 1-Phenyl-N-Methyl-7,8-Dimethoxy-1,2,4,5-Tetrahydrobenzazepines

Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl)-halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine (e.e, 6percent).Coordination of the cyclisation precursor to the tricarbonylchromium(0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-N-methyl-1,2,4,5-tetrahydrobenzazepine. (-)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated cyclisation to furnish trans-(-)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer.In contrast, the epimeric cyclisation precursor (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises to give a mixture (ratio 91:9) of trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine.However, cyclisation of the tricarbonylchromium(0) complex of (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is completely stereoselective to yield trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine after decomplexation.