1173107-91-9

Upstream product

• 13565-37-2 trans-4,4'-dimethylchalcone 
• 557-20-0 diethylzinc 
• 21551-47-3 4,4'-Dimethylchalcon 
• 1041477-73-9 C₂₂H₃₁NO₃S 
• 4294-57-9 para-methylphenylmagnesium bromide 

Relevant academic research and scientific papers

Modulation of multifunctional N,O,P ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc and trapping of the zinc enolate

In this work, we have successfully synthesized a new family of chiral Schiff base-phosphine ligands derived from chiral binaphthol (BINOL) and chiral primary amine. The controllable synthesis of a novel hexadentate and tetradentate N,O,P ligand that contains both axial and sp3-central chirality from axial BINOL and sp3-central primary amine led to the establishment of an efficient multifunctional N,O,P ligand for copper-catalyzed conjugate addition of an organozinc reagent. In the asymmetric conjugate reaction of organozinc reagents to enones, the polymer-like bimetallic multinuclear Cu-Zn complex constructed in situ was found to be substrate-selective and a highly excellent catalyst for diethylzinc reagents in terms of enantioselectivity (up to >99 % ee). More importantly, the chirality matching between different chiral sources, C2-axial binaphthol and sp3-central chiral phosphine, was crucial to the enantioselective induction in this reaction. The experimental results indicated that our chiral ligand (R,S,S)-L1- and (R,S)-L4-based bimetallic complex catalyst system exhibited the highest catalytic performance to date in terms of enantioselectivity and conversion even in the presence of 0.005 mol % of catalyst (S/C=20 000, turnover number (TON)=17 600). We also studied the tandem silylation or acylation of enantiomerically enriched zinc enolates that formed in situ from copper-L4-complex-catalyzed conjugate addition, which resulted in the high-yield synthesis of chiral silyl enol ethers and enoacetates, respectively. Furthermore, the specialized structure of the present multifunctional N,O,P ligand L1 or L4, and the corresponding mechanistic study of the copper catalyst system were investigated by 31P NMR spectroscopy, circular dichroism (CD), and UV/Vis absorption. Match maker: The chiral bimetallic multinuclear Cu-Zn complex that contains a novel phosphine ligand and bears matching axial and sp3-central chirality from binaphthol and chiral amine was found to be a highly efficient catalyst in the enantioselective conjugate addition of an organic zinc reagent. Copyright

Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones

An enantioselective Cu(II)-catalyzed conjugate addition of dialkylzinc reagents to α,β- or α,β,γ,δ-unsaturated ketones with chiral cyclohexane-based amidophosphine ligands was developed. With 2 mol% of Cu(OAc)2·H2O/L5, the conjugate

Convenient access to β-substituted chiral phenones

A highly enantioselective approach towards the synthesis of β-substituted chiral ketones by utilizing Grignard reagents was achieved. The (R)- and (S)-antipodes of the target chiral ketones 2a-2k were obtained with up to 100% ee from chiral N-alkanoylcamp