59168-90-0

Upstream product

• 79-21-0 peracetic acid 
• 767-99-7 2-phenylbut-2-ene 
• 768-00-3 (E)-2-phenyl-2-butene 
• 767-99-7 (Z)-2-phenylbut-2-ene 
• 1117-96-0 Diazoethan 
• 98-86-2 acetophenone 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 74-88-4 methyl iodide 

Downstream Products

• 769-59-5 3-phenyl-butan-2-one 
• 4564-83-4 3-acetoxy-2-phenylbutan-2-ol 
• 52089-32-4 3-phenyl-2-butanol 
• 1565-75-9 2-phenyl-2-butanol 
• 56907-39-2 rac-(2R,3S)-3-phenylbutan-2-ol 
• 59115-85-4 (2RS,3SR)-3-deuterio-3-phenyl-butan-2-ol 

Relevant academic research and scientific papers

Stereospecific Synthesis of Optically Active Phenylpropylene Oxides

The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-α-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated

Titanocene(III)-Catalyzed Precision Deuteration of Epoxides

We describe a titanocene(III)-catalyzed deuterosilylation of epoxides that provides β-deuterated anti-Markovnikov alcohols with excellent D-incorporation, in high yield, and often excellent diastereoselectivity after desilylation. The key to the success of the reaction is a novel activation method of Cp2TiCl2 and (tBuC5H4)2TiCl2 with BnMgBr and PhSiD3 to provide [(RC5H4)2Ti(III)D] without isotope scrambling. It was developed after discovering an off-cycle scrambling with the previously described method. Our precision deuteration can be applied to the synthesis of drug precursors and highlights the power of combining radical chemistry with organometallic catalysis.

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation

The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.

Asymmetric epoxidation of conjugated olefins with dioxygen

A complex situation: Asymmetric epoxidation of conjugated olefins was achieved at room temperature using ruthenium complex 1 as the catalyst and air as the oxidant to give epoxides in up to 95 % ee (see scheme). When the product was acid sensitive, the reaction was carried out at 0 °C under oxygen. Copyright

Photopromoted Ru-catalyzed asymmetric aerobic sulfide oxidation and epoxidation using water as a proton transfer mediator

Ru(NO)-salen complexes were found to catalyze asymmetric aerobic oxygen atom transfer reactions such as sulfide oxidation and epoxidation in the presence of water under visible light irradiation at room temperature. Oxidation of sulfides including alkyl aryl sulfides and 2-substituted 1,3-dithianes using complex 2 as the catalyst proceeded with moderate to high enantioselectivity of up to 98% ee, and epoxidation of conjugated olefins using complex 3 as the catalyst proceeded with good to high enantioselectivity of 76-92% ee. Unlike biological oxygen atom transfer reactions that need a proton and electron transfer system, this aerobic oxygen atom transfer reaction requires neither such a system nor a sacrificial reductant. Although the mechanism of this oxidation has not been completely clarified, some experimental results support the notion that an aqua ligand coordinated with the ruthenium ion serves as a proton transfer agent for the oxygen activation process, and it is recycled and used as the proton transfer mediator during the process. Thus, we have achieved catalytic asymmetric oxygen atom transfer reaction using molecular oxygen that can be carried out under ambient conditions.

Highly enantioselective biphasic iminium-catalyzed epoxidation of alkenes. on the importance of the counterion and of N(sp2)-C(sp3) Rotamers

Diastereomeric biaryliminium cations made of an (Ra)-5,5′,6,6′, 7,7′,8,8′-octahydrobinaphthyl core and exocyclic appendages derived from (S)or (R)-3,3-dimethylbutan-2-amine are effective asymmetric epoxidation catalysts for unfunctionalized alkenes. Herei

Probing competitive enantioselective approach vectors operating in the Jacobsen-Katsuki epoxidation: A kinetic study of methyl-substituted styrenes

This paper describes a study of reactivity and enantioselectivity for a series of methyl-substituted styrenes in the Jacobsen-Katsuki (Mn(salen)-catalyzed) epoxidation reaction. Competition experiments provided kinetic data for the reactivity of the seven possible methyl-substituted styrenes (mono-, di- and trisubstituted) relative to styrene itself, ee values were measured by chiral GC, and absolute configurations were secured by chemical correlation. Of particular interest was the switch in absolute configuration at the benzylic position of the epoxides derived from (Z)- and (E)-α,β-dimethylstyrene, respectively. The results could be rationalized in terms of an approach vector with the phenyl substituent proximal to the salen. As opposed to alkyl groups, a proximal phenyl group has very little effect on the rate of the reaction. Consideration of distal vs proximal approach allows prediction of absolute stereochemistry as a function of alkene substitution pattern. Trisubstituted alkenes with one phenyl group cis to the alkene hydrogen can be identified as a favored substrate class in the title reaction, with both rate and selectivity close to the classic (Z)-β-substituted styrene substrates.

[60]Fullerene supported on silica and γ-alumina sensitized photooxidation of olefins: Chemical evidence for singlet oxygen and electron transfer mechanism

Fullerene C60 supported on silica and γ-alumina (2% w/w C60/SiO2 and C60/Al2O3) sensitizes the photooxidation of alkenes via singlet oxygen and/or electron transfer mechanism, depending on

Catalytic asymmetric epoxidation

A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.