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; Lei Shi; Kang Fu

doi:10.1016/j.cclet.2021.10.062

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
, Lei Shi^*
, Kang Fu

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2415-2419
Number of pages	5
Journal	Chinese Chemical Letters
Volume	33
Issue number	5
DOIs	https://doi.org/10.1016/j.cclet.2021.10.062
State	Published - May 2022
Externally published	Yes

Keywords

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

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@article{64e97dfefed140729b5423392409dd4c,

title = "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",

abstract = "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.",

keywords = "Chiral bisoxazoline ligand, Chiral pocket, Chiral spiro ligand, Friedel-Crafts reaction, Trifluoromethylated all-carbon quaternary stereocenter",

author = "Bao, \{Robert Li Yuan\} and Lei Shi and Kang Fu",

note = "Publisher Copyright: {\textcopyright} 2021",

year = "2022",

month = may,

doi = "10.1016/j.cclet.2021.10.062",

language = "英语",

volume = "33",

pages = "2415--2419",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

number = "5",

}

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. / Bao, Robert Li Yuan; Shi, Lei; Fu, Kang.
In: Chinese Chemical Letters, Vol. 33, No. 5, 05.2022, p. 2415-2419.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters

T2 - Chiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

AU - Bao, Robert Li Yuan

AU - Shi, Lei

AU - Fu, Kang

PY - 2022/5

Y1 - 2022/5

N2 - 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.

AB - 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.

KW - Chiral bisoxazoline ligand

KW - Chiral pocket

KW - Chiral spiro ligand

KW - Friedel-Crafts reaction

KW - Trifluoromethylated all-carbon quaternary stereocenter

UR - https://www.scopus.com/pages/publications/85119580399

U2 - 10.1016/j.cclet.2021.10.062

DO - 10.1016/j.cclet.2021.10.062

M3 - 文章

AN - SCOPUS:85119580399

SN - 1001-8417

VL - 33

SP - 2415

EP - 2419

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 5

ER -