Citation: Robert Li-Yuan Bao, Lei Shi, Kang Fu. Highly enantioselective construction of CF₃-bearing all-carbon quaternary stereocenters: Chiral spiro-fused bisoxazoline ligands with 1, 1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction[J]. Chinese Chemical Letters, ;2022, 33(5): 2415-2419. doi: 10.1016/j.cclet.2021.10.062 shu

Highly enantioselective construction of CF₃-bearing all-carbon quaternary stereocenters: Chiral spiro-fused bisoxazoline ligands with 1, 1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

Robert Li-Yuan Bao ^a ,
Lei Shi ^{a, b, c, d, *,} ,
Kang Fu ^a

a.
School of Science, Harbin Institute of Technology, Shenzhen 518055, China
b.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
c.
Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China
d.
School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China

lshi@hit.edu.cn

Received Date: 11 May 2021
Revised Date: 21 October 2021
Accepted Date: 21 October 2021
Available Online: 27 October 2021

Figures(5)

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF₃-β-disubstituted nitroalkene was favorable.
- Chiral bisoxazoline ligand,
- Chiral pocket,
- Chiral spiro ligand,
- Friedel-Crafts reaction,
- Trifluoromethylated all-carbon quaternary stereocenter
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Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Chiral spiro-fused bisoxazoline ligands with 1, 1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

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通讯作者: 陈斌, bchen63@163.com

Highly enantioselective construction of CF₃-bearing all-carbon quaternary stereocenters: Chiral spiro-fused bisoxazoline ligands with 1, 1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction