14212-53-4

Upstream product

• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 4541-87-1 cis-1-phenylpropene oxide 
• 766-90-5 cis-1-phenyl-1-propylene 
• 873-66-5 1-propenylbenzene 
• 637-50-3 1-phenylpropene 
• 14222-20-9 1R,2R-N-methylpseudoephedrine 
• 103-79-7 1-phenyl-acetone 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 160332-15-0 (+)-(1S,2S)-1-phenyl-1-chloro-2-propanol 
• 160332-19-4 (-)-(1R,2R)-1-phenyl-2-chloro-1-propanol 
• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 
• 160332-21-8 (+)-(1S,2S)-1-phenyl-2-chloro-1-propanol 
• 7516-59-8 As-(benzyl)triphenylarsonium bromide 
• 75-07-0 acetaldehyde 

Downstream Products

• 103-79-7 1-phenyl-acetone 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 1572-95-8 (R)-1-phenyl-propan-2-ol 
• 1402850-47-8 N-methyl-N-(4-methyl-5-phenyl-4,5-dihydrobenzo[d]oxepin-2-yl)methanesulfonamide 
• 1402850-48-9 4-methyl-5-phenyl-4,5-dihydrobenzo[d]oxepin-2(1H)-one 
• 120318-52-7 3-phenylhex-5-en-3-ol 
• 39615-80-0 d,l-1-phenyl-2-methyl-4-penten-2-ol 
• 74333-46-3 anti-2-phenyl-5-hexen-3-ol 
• 74333-47-4 phenyl-2 hexene-5 ol-3 
• 698-87-3 3-phenyl-2-propanol 
• 19424-30-7 trans-4-methyl-5-phenyl-1,3-dioxolan-2-one 
• 90-82-4 pseudoephedrine 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 59168-90-0 (2S,3R)-(+)-2-phenyl-2,3-epoxybutane 

Relevant academic research and scientific papers

Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum

(Chemical Equation Presented) Excellent yields and enantioselectivities can be achieved in the molybdenum-bishydroxamic acid catalyzed asymmetric oxidation of olefins in air at room temperature with an achiral oxidant (see scheme; acac = acetylacetonate).

Enantioselective epoxidation of conjugated Z-olefins with newly modified Mn(salen) complex

Chiral Mn(salen) complex 3 bearing a 1-ethyl-1-methyl-propyl group at C3, C3′, C5, and C5′ was found to induce higher asymmetry in the epoxidation of conjugated Z-olefins, especially less nucleophilic ones, in the presence of 4-phenylpyridine N-oxide than

Natural Deep Eutectic Solvents as Performance Additives for Peroxygenase Catalysis

Natural deep eutectic solvents (NADES) are proposed as alternative solvents for peroxygenase-catalysed oxyfunctionalization reactions. Choline chloride-based NADES are of particular interest as they can serve as solvent, enzyme-stabiliser and sacrificial electron donor for the in situ H2O2 generation. This report provides the first proof-of-concept and basic characterisation of this new reaction system. Highly promising turnover numbers for the biocatalysts of up to 200,000 have been achieved.

Chromium catalysed asymmetric alkene epoxidation. Greater selectivity for an E-alkene versus its Z-isomer

E-β-methylstyrene can be asymmetrically epoxidised stoichiometrically with up to 83% ee and catalytically with up to 77% ee by chiral chromium complexes in the presence of phosphine oxides, DMSO or DMF. In all cases the analogous reaction with Z-β-methyls

Substrate enantioselectivity in the rabbit liver microsomal epoxide hydrolase catalyzed hydrolysis of trans and cis 1-phenylpropene oxides. A comparison with styrene oxide

A preferential consumption of the (1S,2S) enantiomer of (±)-trans-1-phenylpropene oxide (3) and of the (1R,2S) enantiomer of cis-1-phenylpropene oxide (5) is observed during the rabbit liver mEH catalyzed hydrolysis of these epoxides. This preference is, respectively, much lower and much higher than that found for the consumption of the (R) enantiomer in the hydrolysis of (±)-styrene oxide. These results are rationalized in terms of the K(M) and V(max) of the respective reactions.

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.

Enantioselective, Stereoconvergent Resolution Copolymerization of Racemic cis-Internal Epoxides and Anhydrides

Unprecedented enantioselective resolution copolymerization of racemic cis-internal epoxides and anhydrides was mediated by dinuclear aluminum complexes with multiple chirality, affording optically active polyesters with two contiguous stereogenic centers, and the unreacted substrates in good enantioselectivity. Unexpected stereoconvergence is observed in this resolution copolymerization, where the selectivity factor for the enantioselective formation of copolymer significantly exceeds the kinetic resolution coefficient based on the unreacted epoxide at various conversions. Catalytic activity and copolymer enantioselectivity are strongly influenced by the phenolate ortho-substituents of the ligand set, as well as the axial linker and its chirality. An enantiopure binaphthol-linked bimetallic AlIII complex allows stereoconvergent access to the stereoregular semi-crystalline polyesters and a concomitant kinetic resolution of the epoxide substrates.

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

FOx News: Towards Methanol-driven Biocatalytic Oxyfunctionalisation Reactions

The novel formate oxidase from Aspergillus oryzae (AoFOx) is a useful catalyst to promote H2O2-dependent oxyfunctionalisation reactions. In this contribution we exploit the substrate promiscuity of AoFOx to fully oxidise methanol and formaldehyde to CO2 and drive peroxygenase-catalysed stereoselective oxyfunctionalisation reactions. The highly atom efficient H2O2 generation system also enabled high catalytic turnover of the peroxygenase production enzyme.

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.