50778-87-5

Upstream product

• 3524-62-7 benzoin monomethyl ether 
• 67-56-1 methanol 
• 1439-07-2 trans-Stilbene oxide 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 51936-07-3 (+/-)-erythro-α-methoxy-α'-nitryloxy-bibenzyl 

Downstream Products

• 139558-57-9 (+/-)-erythro-α-acetoxy-α'-methoxy-bibenzyl 
• 7476-65-5 (+/-)-erythro-α-methoxy-α'-(4-nitro-benzoyloxy)-bibenzyl 
• 1147-17-7 (1R,2S)-1,2-dimethoxy-1,2-diphenylethane 

Relevant academic research and scientific papers

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.

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.

Selective reductions with stable indium trihydride reagents

The carbene and tertiary phosphine adducts of indane, [InH3{CN(Mes)C2H2N(Mes)}] and [InH3{P(C6H11)3}] (Mes = 2,4,6-trimethylphenyl), have been used to reduce unsaturated organic functionalities. The success and selectivity of these reductions relative to those carried out with lighter group 13 hydride complexes is discussed. (C) 2000 Elsevier Science Ltd.

Preparation of a novel indium hydride and application to practical organic synthesis

Dichloroindium hydride was first generated using the transmetalation between indium trichloride and tributylstannane at - 78 °C, and the generation was confirmed by IR and NMR measurements. The resulting hydride is considerably stable even at ambient temperature due to the coordination of THF, such that it is applicable to practical reduction of carbonyls and halides.

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.

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.