50778-88-6

Upstream product

• 19179-21-6 (+/-)-2r-methoxy-2,3c-diphenyl-oxirane 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 3524-62-7 benzoin monomethyl ether 
• 74-88-4 methyl iodide 
• 645-49-8 cis-stilben 
• 67-56-1 methanol 
• 1439-07-2 trans-Stilbene oxide 
• 1689-71-0 cis-1,2-diphenyloxirane 

Downstream Products

• 139558-57-9 (+/-)-threo-α-acetoxy-α'-methoxy-bibenzyl 
• 22910-73-2 (+/-)-threo-α-ethoxy-α'-methoxy-bibenzyl 
• 115889-24-2 (1R,2R)-2-methoxy-1,2-diphenylethan-1-ol 
• 118353-46-1 (1S,2S)-2-methoxy-1,2-diphenylethan-1-ol 

Relevant academic research and scientific papers

Efficient Rhodium-Catalyzed Hydrogenation of Aldehydes and Ketones

A cationic rhodium(I) catalyst bearing the air-stable and crystalline diphosphine 1,1'-bis-(diisopropylphosphino)ferrocene (1, DiPFc) allows the hydrogenation of aldehydes and ketones under mild conditions.

Highly Enantioselective Ring-Opening of meso-Epoxides with O- and N-Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex

The ring-opening of epoxides is a synthetically significant process widely applied in all kinds of chemistry. Herein, we report the catalytic and highly enantioselective variant of this reaction exploiting our recent endeavors to design and synthesize chi

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

A new series of CuII coordination polymers derived from bis-pyridyl-bis-urea ligands and various dicarboxylates and their role in methanolysis of epoxide ring-opening catalysis

A crystal engineering approach has been adopted in synthesizing six new mixed ligand based CuII coordination polymers (CPs) derived from two bis-pyridyl-bis-urea ligands, namely, N,N′-bis-(3-pyridyl)ethylene-bis- urea (L1) and N,N′-bis-(3-pyridyl)propylene-bis-urea (L2), and various dicarboxylates. The single crystal structures of the coordination polymers displayed diverse supramolecular architectures such as a one-dimensional (1D) chain, 1D-looped chain, and two-dimensional grid. Although none of them displayed an open-framework structure, which is believed to be conducive for heterogeneous catalysis, almost all of them showed moderate to excellent epoxide ring-opening catalysis. Powder X-ray diffraction indicated structural changes/degradation of the CPs, which might be generating substrate accessible CuII species that presumably acted as the catalyst.

Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn

A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O-C/O-N/O-S bonds through a single electron transfer from zinc metal to the niobium-substrate complex due to the high oxophilic nature of the niobium species. The presence of adjacent radical-stabilizing groups is beneficial to epoxide substrates; however the similar prerequisite does not apply to sulfoxides and amine N-oxides, where a broad range of substrates are efficiently deoxygenated in excellent yields.

Generation of hafnium hydride and its application to chemo- and diastereoselective reactions

Hafnium hydride was generated by the transmetalation between Bu 3SnH and HfCl4 using either THF or EtCN as the solvent. This process effectively reduced aldehydes, aldimines, ketones, and esters. In the hafnium hydride reduction of α-alkoxyketones, the diastereoselectivity was dependent on whether THF or EtCN was used as the solvent. Georg Thieme Verlag Stuttgart.

Catalytic monoalkylation of 1,2-diols

A catalytic monoalkylation of 1,2-diols by using a weak base has been developed. Copper(II) dichloride and boronic acids are effective catalysts for activating 1,2-diols in the presence of potassium carbonate as a base. Various 1,2-diols were selectively monoalkylated with allyl-, benzyl- and alkyl- halides in DMF by choosing a suitable catalyst for each 1,2-diols.

Ytterbium trifluoromethanesulfonate Yb(OTf)3: An efficient, reusable catalyst for highly selective formation of β-alkoxy alcohols via ring-opening of 1,2-epoxides with alcohols

Ytterbium(III)triflate-catalysed ring-opening reactions of epoxides derived from styrene, cyclohexene, norbornene and stilbene, in the presence of alcohols (C1-C4 1°, 2° and 3° aliphatic alcohols, cyclohexyl alcohol, allyl and propargyl alcohol) resulted in the formation of β-alkoxy alcohols in good to excellent yield with high regio-, and, where applicable, stereoselectivity. Reaction of stilbene oxide with methanol in the presence of the diethyl ester of L-(+)-tartaric acid afforded the threo form of 1,2-diphenyl-2-methoxy ethanol with high diastereoselectivity (de 94%). Mechanistic implications of the results are discussed.

Reduction of Aromatic Carbonyl Compounds Promoted by Titanium Trichloride in Basic Media. Stereochemistry Studies

Aromatic ketones, which are not affected by Ti(III) chloride in acidic medium, react smoothly in basic media to afford the reductively coupled products according to the increase of the reducing power of Ti(III) ion with increasing pH.Benzil, benzoin, and methoxybenzoin give the corresponding alcohols.The observed stereochemistry is discussed in terms of intermolecular Ti bridging control (dl > meso) when intramolecular Ti complexation is prevented and in terms of steric control (meso > dl) when two sites of potential Ti complexation are available in the molecule.Thereagent, Ti(III) chloride, is selective in that many other functional groups are unaffected by it.