78148-21-7

Upstream product

• 72053-04-4 methyl 2-acetylamino-3-(3,4-dimethoxyphenyl)-2-propenoate 
• 38879-47-9 (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone 
• 100719-08-2 α-Acetamino-β-(3,4-dimethoxy-phenyl)-acrylsaeure-methylester 
• 39740-33-5 carboxymethyl-1 N-acetyl-2 (dihydroxy-3,4 phenyl)-3 alanine 
• 74-88-4 methyl iodide 
• 78083-80-4 (S)-2-amino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 523-02-4 (S)-(-)-norcoralydine 
• 6872-27-1 (R)-(+)-xylopinine 
• 78083-82-6 methyl 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylene-2-veratroylisoquinoline-3-carboxylate 

Relevant academic research and scientific papers

Easy access to drug building-blocks through benzylic C-H functionalization of phenolic ethers by photoredox catalysis

A visible light-mediated photocatalyzed C-C-bond forming method for the benzylic C-H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy is reported. This method allows the mild, selective generation of benzyl radicals in phenolic complex molecules and drug-like compounds, providing new entries in synthetic and medicinal chemistry.

Synthesis of a new bulky phosphite ligand and its application in the enantioselective hydrogenation

A new bulky phosphite ligand was synthesized and tested in the asymmetric Rh-catalyzed hydrogenation of a series of substrates, including dimethyl itaconate (up to 95% ee), α- and β-dehydroamino acid derivatives (up to 88% and 76% ee, respectively). In th

Synthesis of new chiral amidophosphite ligands and their application in hydrogenation of benzodiazepinones and enamides

New chiral amidophosphites were synthesized and tested in the Ir-catalyzed hydrogenation of 4-substituted 1,3-dihydro-2H-1,5-benzodiazepin-2-ones and Rh-catalyzed hydrogenation of dehydro amino acid derivatives. The triphenylphosphine additive can considerably increase the enantioselectivity of both processes.

Chiral Rh phosphine-phosphite catalysts immobilized on ionic resins for the enantioselective hydrogenation of olefins in water

The asymmetric hydrogenation of prochiral enamides with Rh complexes bearing chiral phosphine-phosphite ligands (P-OP) supported on sulphonated polystyrene resins has been studied. The complexes have been supported by simple treatment of preformed [Rh(dio

Practical enantioselective hydrogenation of α-aryl- and α-carboxyamidoethylenes by rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl) (phenyl)phosphino]ethane}

The rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl)(phenyl)phosphino]ethane} [Rh(I)-(t-Bu-SMS-Phos)] catalyst system displayed prime efficiency in the hydrogenation of large series of aamidostyrenes and a-amidoacrylates. Up to >99.9% enantiomeric excesses coupl

Asymmetric hydrogenation of methyl (Z)-2-acetamido-3-(3,4-dimethoxyphenyl) acrylate catalyzed by Rh complexes with available amidophosphite ligands

A convenient express procedure for the preparation of methyl (Z)-2-acetamido-3-(3,4-dimethoxyphenyl)acrylate was developed. Asymmetric hydrogenation of this substrate in the presence of rhodium catalysts involving synthetically available amidophosphite li

Modular monodentate phosphoramidite ligands for rhodium-catalyzed enantioselective hydrogenation

A new class of monodentate phosphoramidite ligands (DpenPhos) has been developed on the basis of the modular concept for Rh(I)-catalyzed asymmetric hydrogenations of a variety of olefin derivatives, affording the corresponding optically active compounds in excellent yields and enantioselectivities. The ligands have the advantages of facile preparation, tunable structure, and broad scope of substrates in their Rh(I) complex-catalyzed asymmetric hydrogenations. Copyright

Highly enantioselective hydrogenation of enamides and itaconic acid in water in the presence of water-soluble rhodium(I) catalyst and sodium dodecyl sulfate

The water-soluble cationic Rh complexes, such as [Rh(α-D- glucopyranosyl-(1,1)-2,3-di-O-(diphenylphosphino)-α-D- glucopyranoside)(cod)]BF4 (1) and [Rh(β-D-glucopyranosyl-(1,1)-2,3-di-O- (diphenylphosphino)-β-D-glucopyranoside)(cod)]BF4 (2) bearing free hydroxy groups, are effective catalysts in the asymmetric hydrogenation of various enamides and itaconic acid (up to 99.9% ee) in water in the presence of sodium dodecyl sulfate (SDS) (7.5 x 10-3 to 1.0 x 10-1 M). The hydrogenation of methyl (Z)-α-acetamidocinnamate in water using the corresponding Rh complexes of triflate (6) and D-camphor-10-sulfonate (7), prepared separately, results in a formation of the product of the same enantioselectivity (48% ee), but the use of SDS can reduce the amount of the catalyst and improve the enantioselectivity to 81% ee. These results show that the counteranions do not directly influence the enantioselectivity. Although the effect of SDS on the enhancement of enantioselectivity remains speculative, the formation of micelle seems to play an important role in improving the enantioselectivity.

Asymmetric hydrogenation - Influence of the structure of carbohydrate derived catalysts on the relative enantioselectivity Q(H/Me) regarding acid and ester substrates and its inversion - Selectivity increase in water by amphiphiles

4,6-O-Benzylidene protected 2,3-bis(O-diphenylphosphino)-D-glycopyranoside rhodium(I) chelate precatalysts 1-4 e,f showed for the hydrogenation of methyl (Z)2-N-acylamidoacrylates 6-8 a stepwise decrease of the enantioselectivity with increasing number of axially oriented hexopyranoside substituents. The decrease is even stronger for the analogous substrate acids 6h-8h resulting in an unusual low relative enantioselectivity Q = q(H)/q(Me) of 0.3 for the precatalysts 4e and 4f. Deprotected, 4,6-OH-group bearing catalysts 1-4 g,h generally show smaller differences of %ee in methanol or benzene, however, not in water. Under addition of amphiphiles a in comparison with blanks b the relative enantioselectivity Q = q(a)/q(b) clearly increases for both groups of catalysts in most cases to Q-values between 3 up to 8 - independent of a neutral or ionic nature of the amphiphile.