16460-86-9

Upstream product

• 1145-92-2 (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone 
• 15681-48-8 lithium dimethylcuprate 
• 34999-86-5 2-dimethylamino-1,3-diphenylpenta-3,4-dien-1-one 
• 557-20-0 diethylzinc 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 93-54-9 1-Phenyl-1-propanol 
• 536-74-3 phenylacetylene 
• 75-03-6 ethyl iodide 
• 94-41-7 benzalacetophenone 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 861557-02-0 2-ethyl-1,3-diphenyl-pentan-1-one 
• 78943-81-4 (+/-)-1ξ,3-diphenyl-pent-1-ene 
• 1454-60-0 1,3-diphenyl-pentan-1-one oxime 
• 857973-57-0 2-methyl-1,3-diphenyl-pentan-1-one 
• 1196-58-3 (1-ethylpropyl)benzene 
• 1334680-81-7 (2R,3S,4S)-3-benzyl-2,4-diphenylhexanoic acid 
• 1334680-78-2 (2R,3S,4S)-3-benzoyl-2,4-diphenylhexanoic acid 
• 1334680-79-3 (2R,3S,4R)-2,4-diphenyl-3-((S)-1-phenylpropyl)pyrrolidine 
• 1334680-76-0 (3R,4S)-3,5-diphenyl-4-((S)-1-phenylpropyl)-3,4-dihydro-2H-pyrrole 
• 1334680-47-5 (2S,3S)-2-((R)-2-nitro-1-phenylethyl)-1,3-diphenylpentan-1-one 
• 861587-17-9 2,2-diethyl-1,3-diphenyl-pentan-1-one 

Relevant academic research and scientific papers

ACCESS TO CHIRAL BISPHENOL (BPOL) LIGANDS THROUGH DESYMMETRIZING ASYMMETRIC ORTHO-SELECTIVE MONO-HALOGENATION

The subject invention pertains to a method of halogenating phenols, yielding a range of halogenated phenols with enantiomeric ratio of up to 99.5:0.5. In certain embodiments, the subject invention pertains to a method of asymmetric halogenation of bisphen

Palladium-catalyzed diastereoselective cross-coupling of two aryl halidesviaC-H activation: synthesis of chiral eight-membered nitrogen heterocycles

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles has been developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represent a novel type of chiral scaffold, which feature easy modification and high configurative stability and have the potential to be applied in asymmetric synthesis. Palladacycles that were formedviathe C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provides a new strategy for the synthesis of medium-sized ring compounds.

Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones

A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,

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.

Mechanistic-Insight-Driven Rate Enhancement of Asymmetric Copper-Catalyzed 1,4-Addition of Dialkylzinc Reagents to Enones

The combination of [Cu(MeCN)4]TFA·TFAH (TFA = O2CCF3) with Feringa's phosphoramidite ligand (LA) provides an exceptionally active (0.75 mol %) catalyst for asymmetric conjugate additions of ZnR2 (R = Et and Me at -40 to -80 °C) to enones. Kinetic and other studies of the addition of ZnEt2 to cyclohex-2-en-1-one indicate a transition state stoichiometry composition of (ZnEt2)3(enone)4Cu2(LA)3 that is generated by transmetalation from Et2Zn(enone)2. Catalyst genesis is significantly slower than turnover (which has limited previous attempts to attain useful kinetic data); in the initial stages, varying populations of catalytically inactive, off-cycle, species are present. These issues are overcome by a double-dose kinetic analysis protocol. A rest state of [LACu(Et)(μ-TFA)(μ-{(enone)(ZnEt)2(enolate)})CuLA2]+ (through the equivalence of enolate = enone + ZnEt2) is supported by DFT studies (ωB97X-D/SRSC). Rate-determining ZnEt2(enone)2 transmetalation drives the exceptionally high catalytic activity of this system.

EBINOL axial chiral compound as well as synthesis method and application thereof

The invention belongs to the field of axial chiral compounds, and discloses an EBINOL axial chiral compound. The EBINOL axial chiral compound has the following general formula(the formula is shown inthe description), wherein R and R are respectively

Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/ Z-Isomerization, Regioselectivity, and Synthetic Applications

The chiral bisphosphine dioxide-catalyzed asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones. Conjugate reduction is accelerated in the presence of an electron-rich aryl group at the β-position of the enone owing to its carbocation-stabilizing ability. Computational studies were also conducted in order to elucidate the origin of the observed enantioselectivity. The regio- and enantioselective reductions of dienones were realized and applied to the syntheses of ar-turmerone, turmeronol A, mutisianthol, and jungianol, which are optically active sesquiterpenes.

Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones

Enantioselective conjugate hydrosilylation of β,β-disubstituted α,β-unsaturated ketones was realized. In the presence of a chiral picolinamide-sulfonate Lewis base catalyst, the reactions provided various chiral ketones bearing a chiral center at the β-po

Enantioselective Cu-catalyzed 1,4-additions of organozinc and Grignard reagents to enones: Exceptional performance of the hydrido-phosphite-ligand BIFOP-H

Enantioselective Cu(I),(II)-(i.e. CuCl, CuCl2, Cu(OTf)2)-catalyzed 1,4-additions of organozinc, i.e. (Et, Me)2Zn, and Grignard reagents, i.e. (Et, Me)MgBr, to chalcone, cyclohexenone and chromone are studied, employing fencholate-based phosphorus ligands, e.g. biphenyl-2,2′-bisfenchyl hydrido phosphite = BIFOP-H. The CuCl·BIFOP-H-catalyzed 1,4-addition of Et2Zn to chalcone yields up to 93% and 99% ee, exceeding established BINOL- and TADDOL-based phosphoramidite ligands. Remarkably, CuCl performs better in 1,4-additions to chalcone (CuCl: 76% ee; Cu(OTf)2: 49% ee; CuCl2: 42% ee) while Cu(OTf)2 performs better in 1,4-additions to cyclohexenone (Cu(OTf)2: 65% ee; CuCl: 20% ee). The computation of the reaction pathway is done for the CuI-catalyzed 1,4-addition to chalcone (CuII will be in situ reduced to CuI by a reagent, TPSS-D3(BJ)/def2-TZVP//B3LYP-D3(BJ)/def2-SVP) for six different model ligands, i.e. (MeO)2P-X (X = H, F, Me, OMe, NMe2 and PMe3). Origins of enantioselectivities are analyzed (M06-2X-D3/def2-TZVP//B3LYP-D3(BJ)/def2-SVP) for transition structures of the 1,4-methylation of chalcone with the Cu·BIFOP-H catalyst and explain the experimentally observed (R)-enantiomer's preference.