70878-24-9

Upstream product

• 64-17-5 ethanol 
• 1009-67-2 2-methyl-3-phenylpropionic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 7042-33-3 ethyl (E)-2-methyl-3-phenyl-2-propenoate 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 100-51-6 benzyl alcohol 
• 7042-33-3 ethyl 2-methylcinnamate 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 34666-01-8 ethyl 2-methyl-3-phenylpropionate 
• 1009-67-2 2-methyl-3-phenylpropanoic acid 
• 70836-92-9 (S)-3-phenyllactic acid ethyl ester p-toluenesulfonate 
• 917-54-4 methyllithium 
• 104910-33-0 ((Z)-1-Ethoxy-3-phenyl-propenyloxy)-trimethyl-silane 
• 140-88-5 ethyl acrylate 

Downstream Products

• 1253042-17-9 3-(4-methoxyphenyl)-1-phenethyl-5-phenyl-1H-pyrrol-2(5H)-one 
• 74669-82-2 (R)-2,3 -dimethyl-4-phenylbutan-2-ol 

Relevant academic research and scientific papers

Indene Derived Phosphorus-Thioether Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Olefins with Diverse Substitution Patterns and Different Functional Groups

A family of phosphite/phosphinite-thioether ligands have been tested in the Ir-catalyzed asymmetric hydrogenation of a range of olefins (50 substrates in total). The presented ligands are synthesized in three steps from cheap indene and they are air-stable solids. Their modular architecture has been crucial to maximize the catalytic performance for each type of substrate. Improving most Ir-catalysts reported so far, this ligand family presents a broader substrate scope, covering different substitution patterns with different functional groups, ranging from unfunctionalized olefins, through olefins with poorly coordinative groups, to olefins with coordinative functional groups. α,β-Unsaturated acyclic and cyclic esters, ketones and amides werehydrogenated in enantioselectivities ranging from 83 to 99% ee. Enantioselectivities ranging from 91 to 98% ee were also achieved for challenging substrates such as unfunctionalized 1,1′-disubstituted olefins, functionalized tri- and 1,1′-disubstituted vinyl phosphonates, and β-cyclic enamides. The catalytic performance of the Ir-ligand assemblies was maintained when the environmentally benign 1,2-propylene carbonate was used as solvent. (Figure presented.).

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.

Pyrrolidine-Based P,O Ligands from Carbohydrates: Easily Accessible and Modular Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Olefins

The potential of P,O-iminosugar based ligands in the Ir-catalyzed asymmetric hydrogenation of minimally functionalized olefins is presented. These new ligands were prepared from easily available carbohydrates (D-mannose, D-ribose and D-arabinose). The stereochemical and polyfunctional diversity of carbohydrates allowed the modulation of the ligands, both from their electronic properties and the rigidity of their backbone. High enantioselectivities (ee’s up to 99 %) can be reached in the hydrogenation of selected tri- and disubstituted substrates.

Iridium catalysts with Chiral bicyclic pyridine-phosphane ligands for the asymmetric hydrogenation of olefins

New bicyclic pyridine-phosphane ligands were prepared, and their iridium complexes were evaluated in asymmetric hydrogenation of trisubstituted olefins with non-coordinating and weakly coordinating substituents. The iridium catalysts showed high reactivity and enantioselectivity for both types of olefins. New pyridine-derived N,P-chelated iridium catalysts were prepared and evaluated in the asymmetric hydrogenation of trisubstituted olefins. High conversions and enantioselectivities were obtained. Copyright

Synthesis of iridium and rhodium complexes with new chiral phosphine-NHC ligands based on 1,1′-binaphthyl framework and their application in asymmetric hydrogenation

The first series of chiral phosphine-imidazole carbene ligands based on a 1,1′-binaphthyl framework were synthesized from (R)-2-amine-2′- (diphenylphosphino)-1,1′-binaphthyl (1) in a four-step pathway. After deprotonation of these phosphine-imidazolium sa

Influence of the position of the substituent on the efficiency of lipase-mediated resolutions of 3-aryl alkanoic acids

Hydrolase-catalysed kinetic resolutions to provide enantioenriched α-substituted 3-aryl alkanoic acids are described. (S)-2-Methyl-3- phenylpropanoic acid (S)-1a was prepared in 96% ee by Pseudomonas fluorescens catalysed ester hydrolysis, while, Candida antarctica lipase B (immob) resolved the α-ethyl substituted 3-arylalkanoic acid (R)-1b in 82% ee. The influence of the position of the substituent relative to the ester site on the efficiency and enantioselectivity of the biotransformation is also explored; the same lipases were found to resolve both the α- and β-substituted alkanoic acids. Furthermore, the steric effect of substituents at the C2 stereogenic centre relative to that for their C3 substituted counterparts on the efficiency and stereoselectivity is discussed.

Asymmetric hydrogenation of α,β-unsaturated carboxylic esters with chiral iridium N,P ligand complexes

Enantioselective conjugate reduction of a wide range of α,β-unsaturated carboxylic esters was achieved using chiral Ir N,P complexes as hydrogenation catalysts. Depending on the substitution pattern of the substrate, different ligands perform best. α,β-Unsaturated carboxylic esters substituted at the α position are less problematic substrates than originally anticipated and in some cases α-substituted substrates actually reacted with higher enantioselectivity than their β-substituted analogues. The resulting saturated esters with a stereogenic center in the α or β position were obtained in high enantiomeric purity. Copyright

Chiral imidate-ferrocenylphosphanes: Synthesis and application as P,N-ligands in iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins

A small library of chiral imidate-ferrocenylphosphane ligands was efficiently synthesized (8 examples) and evaluated in the iridium(i)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins. These catalysts perform very well in a range of examples (yields and ee's up to 100%).

Recent advances in iridium-catalyzed asymmetric hydrogenation: New catalysts, substrates and applications in total synthesis

Iridium-catalyzed asymmetric hydrogenation has emerged as a highly efficient method for the synthesis of enantiomerically pure compounds. This account summarizes our recent efforts in this field. We have developed a new type of P,O-ligand that was success

Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters

α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright