Copper (I)‐BOX Catalyzed Asymmetric 3‐Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines

An asymmetric 3‐component reaction between EthynylBenziodoXoles (EBXs), 2,2,2‐trifluorodiazoethane and nucleophiles catalyzed by a CuI‐BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and anilines, which are valuable building blocks...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-08, Vol.62 (32), p.e202305776-n/a
Main Authors: Ramirez, Nieves P., Waser, Jerome
Format: Article
Language:English
Subjects:
Alcohols
Alkynes
Aniline
Asymmetric Catalysis
Asymmetry
Catalysts
Chemical synthesis
Enantiomers
Ethers
Fluorinated Diazo Compounds
Multi-Component Reactions
Nucleophiles
Stereoselectivity
Substrates
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Summary:An asymmetric 3‐component reaction between EthynylBenziodoXoles (EBXs), 2,2,2‐trifluorodiazoethane and nucleophiles catalyzed by a CuI‐BOX (Bisoxazoline) catalyst is described. This protocol gives access to chiral trifluoromethylated propargyl ethers and anilines, which are valuable building blocks in synthetic and medicinal chemistry. The reaction proceeds with high enantioselectivity and yield with different nucleophiles such as primary, secondary and tertiary alcohols, as well as both electron‐rich and electron‐poor anilines. Aryl‐, alkyl‐ and silyl‐substituted alkynes can be successfully introduced as electrophiles. In case of chiral substrates, high catalyst control was observed, leading to good diastereoselectivity. The asymmetric synthesis of trifluoromethylated propargylic ethers and amines is described. The reaction proceeds with high enantioselectivity using a simple chiral CuI‐BOX system and tolerates a broad range of alcohol, aniline and alkyne substitution. With chiral alcohols, a high diastereoselectivity is observed, indicating good catalyst stereocontrol.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202305776