96687-73-9

Upstream product

• 186581-53-3 diazomethane 
• 93-25-4 2-methoxyphenylacetic acid 
• 60779-19-3 Methyl (+/-)-2-(2-Methoxyphenyl)propanoate 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 
• 529-28-2 4-iodoanisol 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 81616-80-0 (S)-2-(2-methoxyphenyl)-propionic acid 
• 77-78-1 dimethyl sulfate 
• 81616-75-3 2-methoxy-α-methylene-benzeneacetic acid 
• 81616-76-4 2-(2-methoxyphenyl)propenoic acid ethyl ester 
• 66644-69-7 ethyl (2-methoxyphenyl)(oxo)acetate 
• 578-57-4 2-bromoanisole 

Downstream Products

• 96641-45-1 (S)-2-methoxy-β-methylbenzeneethanol 
• 96641-49-5 (S)-(+)-1-Acetoxy-2-(2-hydroxyphenyl)propane 
• 96641-47-3 Acetate of (S)-(+)-2-(2-methoxyphenyl)-1-propanol 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Pd/Josiphos-catalyzed enantioselective α-arylation of silyl ketene acetals and mechanistic studies on transmetalation and enantioselection

Palladium/(4-MeO-3,5-MePh)2PF-Pcy2) catalyzed the enantioselective arylation of silyl ketene acetals with iodoarenes in the presence of TlOAc to promote transmetalation of silyl ketene acetals. The highest enantioselectivities giving α-arylesters up to 91% ee were achieved when (E)-1-methoxy-1-(trimethylsiloxy)propene (E/Z = 88/12) was used for the silyl ketene acetal. The effect on enantioselection of a chiral ligand is discussed on the basis of the X-ray structure of the palladium/(4-MeO-3,5- MePh)2PF-Pcy2) complex and results of DFT computational studies on mechanistic aspects of the catalytic cycle.

ENZYMATIC RESOLUTION OF METHYL 2-ALKYL-2-ARYLACETATES

Horse liver esterase, used as its inexpensive commercial acetone powder, catalyzes the selective hydrolysis of methy 2-alkyl-2-arylacetates to afford R(-)-2-alkyl-2-arylacetic acids and S(+)-methyl 2-alkyl-2-arylacetates.

The Total Synthesis of (15R)- and (15S)-16-Hydroxyferruginol

In order to assign the absolute configuration of C-15 in natural 16-hydroxyferruginol, (5S,10S,15R)-(1a) and (5S,10S,15S)-8,11,13-abietatriene-12-16-diol (1b) have been synthesized.Optical resolution of 2-(2-methoxyphenyl)propanoic acid, prepared from methyl (2-methoxyphenyl)acetate, with cinchonidine afforded (R)- and (S)-enantiomers, which were converted into triphenylphosphonium chloride (3a) and its (S)-isomer (3b) respectively.The Wittig reaction of (R)-(-)-α-cyclocitral with 3a, followed by partial catalytic hydrogenation and intramolecular cyclization gave (5S,10S,15R)-12,16-dimethoxy-8,11,13-abietatriene (16a) together with its (5S,10R,15R)-isomer.Similary, 3b was also converted into (5S,10S,15S)-12,13-dimethoxy-8,11-abietatriene (6b) and its (5S,10R,15R)-isomer.Demethylation of 16a gave 1a which was identical with natural 16-hydroxyferruginol.The dimethoxy compound 16b was also demethylated to give 1b.