100018-61-9

Upstream product

• 116652-87-0 (2R)-1-((S)-2-methoxymethylpyrrolidino)-2-phenyl-2-propanol 
• 98-83-9 isopropenylbenzene 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 627076-70-4 (R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate 
• 20780-53-4 (R)-Styrene oxide 
• 74-88-4 methyl iodide 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 70775-39-2 dimethylsulfoxonium methylide 
• 98-86-2 acetophenone 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 591-51-5 phenyllithium 
• 2406-23-7 (R)-ethyl 2-hydroxy-2-phenylpropanoate 
• 131982-01-9 (R)-1-((S)-2-Hydroxy-1-phenyl-ethylsulfanyl)-2-phenyl-propan-2-ol 

Downstream Products

• 53777-08-5 (S)-2-phenyl-butan-2-ol 
• 37778-99-7 (S)-2-phenyl-1-propanol 
• 98-83-9 isopropenylbenzene 
• 34713-70-7 2-Phenylpropanal 
• 1123-85-9 (+)-(R)-2-phenylpropanol 
• 93-53-8 (S)-2-phenyl-propionaldehyde 
• 93-53-8 (R)-2-phenylpropanal 

Relevant academic research and scientific papers

A new, facile method to prepare hybrid calcium poly(styrene-phenylvinylphosphonate)-phosphate materials for a superior performance catalyst support

A simple and facile route is developed to synthesize a new type of calcium poly(styrene-phenylvinylphosphosphonate)-phosphate (CaPS-PVPA). Structure analysis reveals that CaPS-PVPA is a layered crystalline mesoporous material and could have potential appl

Biomimetic non-heme iron-catalyzed epoxidation of challenging terminal alkenes using aqueous H2O2 as an environmentally friendly oxidant

Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.

Stable chiral salen Mn(III) complexes with built-in phase-transfer capability for the asymmetric epoxidation of unfunctionalized olefins using NaOCl as an oxidant

A series of novel chiral salen Mn(III) complexes with inherent phase-transfer capability were prepared by covalent linkage of the limidazolium IL moieties containing various PEG chains with chiral salen ligand at two sides of 5,5′-position. Technologies of characterization well suggested the presence of polyether chain, the IL linker, and the intact active sites in the complexes. The amphipathic nature of the PEG chain allowed the PEG-based catalysts to undergo built-in phase transfer, which in turn increased the reaction rates in water/organic biphasic systems. Enantioselective epoxidation of styrene, α-methylstyrene, indene, 1,2-dihydronaphthalene, 6-cyano-2,2-dimethylchromene, and 6-nitro-2,2-dimethylchromene catalyzed by the complexes with NaOCl gave >99% conversions within 60 min. The enantiomeric excess (ee) for the epoxides was in the range of 68-93%, except for styrene (ee, 35%) and α-methylstyrene (ee, 42%). Furthermore, the PEG-based complexes were stable and could be separated from the reaction mixture by control of the solvent.

Synthesis and catalytic reactivity of D4-symmetric dinorbornabenzene-derived metallotetraarylporphyrins

The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5: 8-dimethanoanthracene-9-carboxyaldehyde, with pyrrole produced the first chiral tetraarylporphyrin 1 exhibiting D4-symmetry. The resolved benzaldehyde was synthesized in seven steps from p-benzoquinone and cyclopentadiene and included a resolution via diastereomeric ketals. A manganese chloride complex of porphyrin 1 was used as a catalyst for the asymmetric epoxidation of aromatic substituted alkenes in the presence of excess sodium hypochlorite in up to 7,200 turnovers and up to 76% e.e and >90% yield.

An effective strategy for creating asymmetric MOFs for chirality induction: A chiral Zr-based MOF for enantioselective epoxidation

Recently the construction of chiral MOFs (CMOFs) has been very challenging and complex. For the first time, we synthesized a chiral Zr-based MOF with l-tartaric acid by solvent-assisted ligand incorporation (SALI). We show that a CMOF can be postsynthetically generated by a simple method: incorporating chiral carboxylic groups on the achiral NU-1000. The post-synthesized chiral NU-1000 was used as an asymmetric support for producing a chiral catalyst with molybdenum catalytic active centers as Lewis acid sites. Enantioselective epoxidation of various prochiral alkens to epoxids by using [C-NU-1000-Mo] is comparable to that using other asymmetric homogeneous and heterogeneous catalysts, along with high enantiomeric excess and selectivity to epoxide (up to 100%). The CMOF could be reused in the styrene oxidation after five cycles without substantial deterioration in the CMOF crystallinity or catalytic performance.

Iridium-catalyzed alternative of the Meinwald rearrangement

A novel and easy to handle procedure for the regioselective rearrangement of epoxides has been developed, based on an iridium catalyst.

Enhanced enantioselective oxidation of olefins catalyzed by Mn-porphyrin immobilized on graphene oxide

An efficient enantioselective heterogeneous catalyst, GO-[Mn(TPyP)tart], was prepared by covalent attachment of Mn(III) complex of H2TPyP via the propyl linkage to graphene oxide (GO) nanosheet and using chiral tartrate counter ion. The catalyst was characterized by Fourier transform infrared (FT-IR), diffuse reflectance ultraviolet–visible (DR UV–Vis) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy (SEM), Raman and thermogravimetric analysis (TGA). The graphene-supported Mn-porphyrin showed higher activity for the enantioselective epoxidation of unfunctionalized olefins with molecular oxygen in the presence of isobutyraldehyde. It could be recovered easily and reused in asymmetric oxidation of styrene precursor in a five-step sequence without any considerable loss of its catalytic activity and selectivity. The obtained optically epoxide selectivities were achieved in 86% to 100%.

A recyclable Mn-porphyrin catalyst for enantioselective epoxidation of unfunctionalized olefins using molecular dioxygen

A magnetically separable chiral catalyst, Fe3O4/tart/Mn(TCPP)Cl, was prepared by the synthesis and immobilization of manganese-tetra(4-carboxyphenyl)porphyrin, Mn(TCPP)Cl, onto the chiral surface of magnetite nanoparticles (Fe3O4/tart-NPs; tart = l-tartaric acid) through the carboxylate groups. The solid catalyst was characterized by a variety of methods including XRD, FE-SEM, FT-IR and UV-Vis spectroscopy. The catalytic activity was tested in the epoxidation reactions of prochiral olefins with molecular oxygen. The reactions were carried out in acetonitrile as solvent with molecular oxygen in the presence of isobutyraldehyde as the stoichiometric oxidant. The catalyst showed consistently high conversion, selectivity and enantioselectivity to epoxide formation in the oxidation of a variety of terminal, cyclic and aromatic olefins. The catalyst showed little deactivation with time and it is easily recovered by magnetic filtration and could be reused four times with little or no loss in activity and selectivity.

Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita

Here we report on the stereoselective benzylic hydroxylation and C1-C2 epoxidation of alkylbenzenes and styrene derivatives, respectively, by a heme-thiolate peroxygenase (EC 1.11.2.1) from the fungus Agrocybe aegerita. Benzylic hydroxylation led exclusively to the (R)-1-phenylalkanols. For (R)-1-phenylethanol, (R)-1-phenylpropanol and (R)-1-tetralol, the ee reached >99%. For longer chain lengths, the enantiomeric excesses (ee) and total turnover numbers (TTN) decreased while the number of by-products, e.g. 1-phenylketones, increased. Epoxidation of straight chain and cyclic styrene derivatives gave a heterogeneous picture and resulted in moderate to excellent ee values and TTN: e.g., in the case of (1R,2S)-cis-β-methylstyrene oxide formation, an ee >99% and a TTN of 110000 was achieved. Hydroxylation and epoxidation were true peroxygenations, which was demonstrated by the incorporation of 18O from H218O2 into the products. The use of fed-batch devices and varying feeding strategies for the substrate and co-substrate turned out to be a suitable approach to optimize peroxygenase catalysis.

Chiral salen Mn (III) immobilized on ZnPS-PVPA through alkoxyl-triazole for superior performance catalyst in asymmetric epoxidation of unfunctionalized olefins

Chiral salen Mn (III) catalysts anchored onto ZnPS-PVPA via click chemistry are prepared and applied in asymmetric epoxidations of unfunctionalized olefins. Superior catalytic performances (conv%, up to >99; ee%, up to >99) are achieved in the epoxidations of α-methylstyrene, styrene, indene and 1-octene. According to 6-cyano-2,2-dimethylchromene and 6-nitro-2,2-dimethylchromene, configuration of epoxides are reversed. And then the catalysts are selective in not only oxidative systems, but also substrates. Moreover, superior reusability (yield, 82%; ee, 86%) after recycling for nine times could also be obtained, which provide the potential application in industry.