20698-95-7

Upstream product

• 2674-04-6 diphenyl cadmium 
• 68679-84-5 (S)-3-phenyl butyric acid chloride 
• 87258-49-9 (2Ξ,3R)-2-dimethylamino-1,3-diphenyl-butan-1-one 
• 917-54-4 methyllithium 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 75-16-1 methylmagnesium bromide 
• 15681-48-8 lithium dimethylcuprate 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 98-80-6 phenylboronic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 54435-79-9 (E)-1,3-diphenyl-3-methyl-2-propen-1-one 
• 544-97-8 dimethyl zinc(II) 
• 94-41-7 benzalacetophenone 
• 495-45-4 dypnone 

Downstream Products

• 17293-53-7 (S)-1,3-diphenylbutane 
• 4435-52-3 (1R,3S)-1,3-diphenyl-1-butanol 

Relevant academic research and scientific papers

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.

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.

Compartmentalization and Photoregulating Pathways for Incompatible Tandem Catalysis

This contribution describes an advanced compartmentalized micellar nanoreactor that possesses a reversible photoresponsive feature and its application toward photoregulating reaction pathways for incompatible tandem catalysis under aqueous conditions. The

Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel

Nickel-catalyzed asymmetric hydrogenation of several types of alkenes proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. The scope of alkenes herein include α,β-unsaturated esters, n

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.

Rational Design of New Dihydrobenzooxophosphole-Based Lewis Base Organocatalysts

A series of new dihydrobenzooxophosphole-based Lewis base organocatalysts were designed and synthesized. They are shown to be effective in trichlorosilane-mediated stereoselective conjugate reductions of C=C bonds. DFT calculations reveal that the strong

Giving a Second Chance to Ir/Sulfoximine-Based Catalysts for the Asymmetric Hydrogenation of Olefins Containing Poorly Coordinative Groups

This work identifies a family of Ir/phosphite-sulfoximine catalysts that has been successfully used in the asymmetric hydrogenation of olefins with poorly coordinative or noncoordinative groups. In comparison with analogue Ir/phosphine-sulfoximine catalysts previously reported, the presence of a phosphite group extended the range of olefins than can be efficiently hydrogenated. High enantioselectivities, comparable to the best ones reported, have been achieved for a wide range of olefins containing relevant poorly coordinative groups such as α,β-unsaturated enones, esters, lactones, and lactams as well as alkenylboronic esters.

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.