1528-59-2

Upstream product

• 64-17-5 ethanol 
• 55039-36-6 3-phenyl-pent-2-enoyl chloride 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 93-55-0 1-phenyl-propan-1-one 
• 623-51-8 ethyl 2-sulfanylacetate 
• 925-90-6 ethylmagnesium bromide 
• 185987-41-1 (Z)-3-Phenyl-3-phenyltellanyl-acrylic acid ethyl ester 
• 55164-19-7 ethyl-(Z)-3-chloro-3-phenyl-2-propenoate 
• 55164-20-0 ethyl-(E)-3-chloro-3-phenyl-2-propenoate 
• 18819-63-1 (E)-3-chloro-3-phenyl-2-propenoic acid 
• 18819-66-4 (Z)-3-chloro-3-phenyl-2-propenoic acid 
• 55314-57-3 ethyl pent-2-ynoate 
• 98-80-6 phenylboronic acid 
• 183614-20-2 1-(1,2,4-triazol-1-yl)-3-phenylpropargyl ethyl ether 

Downstream Products

• 2845-28-5 (+/-)-3-phenylpentan-1-ol 
• 93-55-0 1-phenyl-propan-1-one 
• 298-12-4 Glyoxilic acid 
• 1239569-08-4 (S)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 
• 67478-54-0 ethyl 3-ethyl-3-phenylpropionate 
• 1613191-09-5 4-ethyl-7-methyl-4-phenylchroman-2-one 
• 1613191-10-8 4-ethyl-6-methyl-4-phenylchroman-2-one 
• 251660-12-5 (R)-3-phenylpentanoic acid ethyl ester 
• 5223-65-4 1,2,3-Trimethyl-1-aethyl-3-phenyl-indan 
• 111583-92-7 1,3-diethyl-1-methyl-3-phenyl-indan 
• 1376710-87-0 (E)-N-methoxy-N-methyl-3-phenylpent-2-enamidee 
• 56422-91-4 (E)-4-phenyl-3-hexen-2-one 
• 1528-58-1 (E)-3-phenyl-2-pentenoic acid 

Relevant academic research and scientific papers

Symbiotic reagent activation: Oppenauer oxidation of magnesium alkoxides by silylglyoxylates triggers second-stage aldolization

The treatment of silylglyoxylates with magnesium alkoxides at ambient temperature results in symbiotic Oppenauer oxidation of the alkoxide and Meerwein-Ponndorf-Verley reduction of the silylglyoxylate. The reduced silylglyoxylate undergoes subsequent [1,2

A rotary molecular motor gated by electrical energy

DFT calculations predict that the chiral pentiptycene derivative E-1 possesses distinct rotational potential energy surfaces in the neutral vs the radical anionic (E-1?-) form such that continued electrochemical switching between E-1 and E-1su

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin

Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.

Catalytic Asymmetric Transfer Hydrogenation of trans-Chalcone Derivatives Using BINOL-derived Boro-phosphates

Chiral phosphoric-acid-catalyzed asymmetric reductions of trans-chalcones have been investigated in this work. A BINOL-derived boro-phosphate-catalyzed asymmetric transfer hydrogenation of the carbon-carbon double bond of trans-chalcone derivatives employing borane as a hydride source was realized. This methodology provides a convenient procedure to access chiral dihydrochalone derivatives in high yields and with high enantioselectivities under mild conditions.

Anti-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis

A general catalytic anti-hydroarylation of electron-deficient internal alkynes compatible with both electron-poor and electron-rich aryl reagents is reported. This selectivity is achieved through a sequential syn-carbopalladation of the alkyne by an Ar-Pd species, followed by a tandem, Ir-photocatalyzed, counter-thermodynamic E → Z isomerization. The use of ortho-substituted boronic acids enables direct access to pharmaceutically relevant heterocyclic cores via a cascade process. Mechanistic insight into the involvement of Ar-Pd versus Pd-H as an active species is provided.

Highly Selective and Catalytic Generation of Acyclic Quaternary Carbon Stereocenters via Functionalization of 1,3-Dienes with CO2

The catalytic asymmetric functionalization of readily available 1,3-dienes is highly important, but current examples are mostly limited to the construction of tertiary chiral centers. The asymmetric generation of acyclic products containing all-carbon quaternary stereocenters from substituted 1,3-dienes represents a more challenging, but highly desirable, synthetic process for which there are very few examples. Herein, we report the highly selective copper-catalyzed generation of chiral all-carbon acyclic quaternary stereocenters via functionalization of 1,3-dienes with CO2. A variety of readily available 1,1-disubstituted 1,3-dienes, as well as a 1,3,5-triene, undergo reductive hydroxymethylation with high chemo-, regio-, E/Z-, and enantioselectivities. The reported method features good functional group tolerance, is readily scaled up to at least 5 mmol of starting diene, and generates chiral products that are useful building blocks for further derivatization. Systemic mechanistic investigations using density functional theory calculations were performed and provided the first theoretical investigation for an asymmetric transformation involving CO2. These computational results indicate that the 1,2-hydrocupration of 1,3-diene proceeds with high π-facial selectivity to generate an (S)-allylcopper intermediate, which further induces the chirality of the quaternary carbon center in the final product. The 1,4-addition of an internal allylcopper complex, which differs from previous reports involving terminal allylmetallic intermediates, to CO2 kinetically determines the E/Z- and regioselectivity. The rapid reduction of a copper carboxylate intermediate to the corresponding silyl-ether in the presence of Me(MeO)2SiH provides the exergonic impetus and leads to chemoselective hydroxymethylation rather than carboxylation. These results provide new insights for guiding further development of asymmetric C-C bond formations with CO2

Enantioselective epoxidation of β,β-disubstituted enamides with a manganese catalyst and aqueous hydrogen peroxide

Enantioselective epoxidation of β,β-disubstituted enamides with aqueous hydrogen peroxide and a novel manganese catalyst is described. Epoxidation is stereospecific and proceeds fast under mild conditions. Amides are disclosed as key functional groups to enable high enantioselectivity.