Citation: Sheng-Jian Jia, Da-Ming Du. Enantioselective chlorination ofb-keto esters and amides catalyzed by chiral copper(Ⅱ) complexes of squaramide-linked bisoxazoline ligand[J]. Chinese Chemical Letters, ;2014, 25(11): 1479-1484. doi: 10.1016/j.cclet.2014.06.023 shu

Enantioselective chlorination ofb-keto esters and amides catalyzed by chiral copper(Ⅱ) complexes of squaramide-linked bisoxazoline ligand

Sheng-Jian Jia ,
Da-Ming Du ^,

1.
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, China

Corresponding author: Da-Ming Du,
Received Date: 24 April 2014
Available Online: 12 June 2014
Fund Project:

Enantioselective chlorination of β-keto esters and amides catalyzed by squaramide-linked bisoxazoline ligand-Cu(OAc)₂ complexes was investigated. The corresponding chlorinated products were obtained in excellent yields with moderate enantioselectivities. The effect of solvent, temperature, Lewis acid, and ligand structure on the reaction is discussed. This was the first investigation of catalytic asymmetric α-chlorination of β-keto amides. This study has highlighted that a simple chiral squaramide-oxazoline with cheap Cu(OAc)₂·H₂O complexes can catalyze this chlorination.
- Asymmetric catalysis,
- Bisoxazoline,
- Squaramide,
- Chlorination,
- β-Keto esters
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