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- W2904123350 endingPage "971" @default.
- W2904123350 startingPage "961" @default.
- W2904123350 abstract "A novel chiral phosphine–urea bifunctional ligand has been developed for Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of iminoesters with methacrylonitrile, a long-standing challenging substrate in asymmetric catalysis. Distortion–interaction energy analysis based on density functional theory (DFT) calculations reveals that the distortion energy plays an important role in the observed enantioselectivity, which can be attributed to the steric effect between the phosphine ligand and the dipole reactant. DFT calculations also indicate that nucleophilic addition is the enantioselectivity-determining step and hydrogen bonding between the urea moiety and methacrylonitrile assists in control of the diastereo- and enantioselectivity. By a combination of metal catalysis and organocatalysis, excellent diastereo- and enantioselectivities (up to 99:1 diastereomeric ratio, 99% enantiomeric excess) as well as good yields are achieved. A wide range of substitution patterns of both iminoester and acrylonitrile is tolerated by this catalyst system, providing access to a series of highly substituted chiral cyanopyrrolidines with up to two quaternary stereogenic centers. The synthetic utility is demonstrated by enantioselective synthesis of antitumor agent ETP69 with a pivotal nitrile pharmacophore and an all-carbon quaternary stereogenic center." @default.
- W2904123350 created "2018-12-22" @default.
- W2904123350 creator A5018125178 @default.
- W2904123350 creator A5026651467 @default.
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- W2904123350 creator A5045157301 @default.
- W2904123350 creator A5054829836 @default.
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- W2904123350 creator A5061609767 @default.
- W2904123350 creator A5084323301 @default.
- W2904123350 creator A5088315391 @default.
- W2904123350 date "2018-12-13" @default.
- W2904123350 modified "2023-10-18" @default.
- W2904123350 title "Well-Designed Phosphine–Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study" @default.
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