115651-75-7

Upstream product

• 557-20-0 diethylzinc 
• 1896-62-4 (E)-benzalacetone 
• 50552-30-2 4-phenyl-5-hexen-2-one 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 67-64-1 acetone 
• 811-49-4 ethyllithium 
• 100-52-7 benzaldehyde 
• 97-93-8 triethylaluminum 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1528-59-2 3-phenyl-pent-2-enoic acid ethyl ester 
• 93-55-0 1-phenyl-propan-1-one 
• 56422-91-4 (E)-4-phenyl-3-hexen-2-one 
• 91667-21-9 (Z)-4-phenyl-3-hexen-2-one 
• 22174-65-8 (Z,E)-4-phenyl-3-hexen-2-one 

Relevant academic research and scientific papers

Functionalized BINOL-mono-PHOS for multinuclear Cu-catalysts in asymmetric conjugate addition of organozinc reagents

Functionalization of BINOL-mono-PHOS achieved the Cucatalyzed highly asymmetric conjugate addition of organozinc reagents to enones. The incorporation of a bulky hydroxy group at the 3'-position of BINOL-mono-PHOS dramatically improved the yield and enantioselectivity. The present novel BINOL-mono-PHOS ligands are effective in the Cu-catalyzed asymmetric conjugate addition of organozinc reagents in both acyclic enones and cyclohexenone.

Diastereomeric phosphite-pyridine ligands for enantioselective 1,4-conjugate additions

Diastereomeric phosphite-pyridine ligands derived from racemic biphenyl units and homochiral BINOL, achieved high enantioselectivities (up to 96.1% ee) in the Cu(I)-catalysed conjugate additions of Et2Zn to a variety of acyclic enones.

A new chiral 2-sulfonylamino-2′-phosphino-1,1′-binaphthyl ligand for highly enantioselective copper-catalyzed conjugate addition of diethylzinc to benzylideneacetones

A new axially chiral phosphine-sulfonamide ligand was prepared via a chiral component (R)-2-amino-2′-diphenylphosphinyl-1,1′-binaphthyl, which was conveniently synthesized through a new route involving hydrolysis of (R)-2-cyano-2′-phosphinyl-1,1′-binaphth

Novel biphenol phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of dialkyl zincs

Phosphoramidite ligands, based on a chiral amine and atropoisomerically flexible biphenols, induce high enantioselectivities (ee's up to 98%) in the copper-catalyzed conjugate addition of dialkyl zinc reagents to a variety of Michael acceptors.

Influence of the double-bond geometry of the Michael acceptor on copper-catalyzed asymmetric conjugate addition

Focusing on mechanistic aspects, a study of the influence of the (E)/(Z) double-bond geometry of the Michael acceptor on the enantioselectivity of copper-catalyzed asymmetric conjugate addition reactions has been realized. In spite of numerous articles co

Readily prepared chiral P,N ligands and their applications in Cu-catalyzed enantioselective conjugate additions

A new type of phosphite-pyridine (P,N) ligand derived from (S)-NOBIN and (S)-BINOL was employed in Cu(I)-catalyzed conjugate addition of diethylzinc to chalcones. The new P,N ligands were highly efficient in the copper-catalyzed enantioselective 1,4-conju

Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones in the presence of planar-chiral phosphaferrocene-oxazoline ligands

(graph presented) A new subclass of chiral phosphaferrocene-oxazoline ligands has been applied to the copper-catalyzed asymmetric conjugate addition of diethylzinc to acyclic enones, furnishing good enantioselectivity. The ligand design readily lends itse

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.

Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions

The asymmetric conjugate addition of dialkylzincs is usually performed with Cu(OTf)2 in toluene. We show that by using a copper carboxylate in Et2O, THF, or EtOAc, we strongly improve the enantioselectivity with a given ligand. Ee va

Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands

The asymmetric conjugate addition of diethyl zinc to cyclohexen-2-one occurs with 0.5% copper (II) triflate and 1% chiral phosphite. Cyclic phosphites derived from various tartrates gave a moderate enantiomeric excess. The nature of the exocyclic substitu