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• W2320436019 endingPage "2253" @default.
• W2320436019 startingPage "2242" @default.
• W2320436019 abstract "Abstract 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 sp 3 ‐central chirality from axial BINOL and sp 3 ‐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, C 2 ‐axial binaphthol and sp 3 ‐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 31 P NMR spectroscopy, circular dichroism (CD), and UV/Vis absorption." @default.
• W2320436019 created "2016-06-24" @default.
• W2320436019 creator A5016648658 @default.
• W2320436019 creator A5018189868 @default.
• W2320436019 creator A5019478505 @default.
• W2320436019 creator A5024385167 @default.
• W2320436019 creator A5024500653 @default.
• W2320436019 creator A5037929437 @default.
• W2320436019 creator A5046927622 @default.
• W2320436019 date "2013-06-18" @default.
• W2320436019 modified "2023-10-18" @default.
• W2320436019 title "Modulation of Multifunctional N,O,P Ligands for Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc and Trapping of the Zinc Enolate" @default.
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