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

Bao，Robert Li Yuan1; Shi，Lei1,2,3,4; Fu，Kang1

2021

10.1016/j.cclet.2021.10.062

CHINESE CHEMICAL LETTERS   影响因子和分区

1001-8417

1878-5964

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-CF-β-disubstituted nitroalkene was favorable.

Chiral bisoxazoline ligand Chiral pocket Chiral spiro ligand Friedel-Crafts reaction Trifluoromethylated all-carbon quaternary stereocenter

SCI

英语

通讯

Chemistry

Chemistry, Multidisciplinary

WOS:000789384800023

ELSEVIER SCIENCE INC

CHEMISTRY

2-s2.0-85119580399

Scopus

1.School of Science,Harbin Institute of Technology,Shenzhen,518055,China
2.State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin,300071,China
3.Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
4.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China

Bao，Robert Li Yuan,Shi，Lei,Fu，Kang. Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction[J]. CHINESE CHEMICAL LETTERS,2021,33(5).

Bao，Robert Li Yuan,Shi，Lei,&Fu，Kang.(2021).Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction.CHINESE CHEMICAL LETTERS,33(5).

Bao，Robert Li Yuan,et al."Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction".CHINESE CHEMICAL LETTERS 33.5(2021).