Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization: access to CF3-containing 2-azaspiro[4.5]decanes.

@article{Han2014CoppercatalyzedIT,
  title={Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization: access to CF3-containing 2-azaspiro[4.5]decanes.},
  author={Guifang Han and Yuxiu Liu and Qingmin Wang},
  journal={Organic letters},
  year={2014},
  volume={16 12},
  pages={
          3188-91
        }
}
Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization was achieved and used to regiospecifically construct a variety of trifluoromethylated 2-azaspiro[4.5]decanes bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields. 
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57 Citations

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Copper‐Catalyzed Intramolecular Trifluoromethylation of N‐Benzylacrylamides Coupled with Dearomatization: Access to CF3‐Containing 2‐Azaspiro[4.5]decanes.
Transformation of the methacrylamide analogue of the acrylamide (Ia) fails to give the corresponding 3-azaspiro[5.5]undecane derivative.
Copper-Catalyzed Phosphonylation/Trifluoromethylation of N-p-NO2-Benzoylacrylamides Coupled with Dearomatization and Denitration.
A novel and efficient copper-tert-butyl hydroperoxide mediated intramolecular spirocyclization of N-p-NO2-benzoylacrylamides through a cascade radical…
Silver-catalyzed carbon-phosphorus functionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to phosphorylated aza-decenones.
Silver-catalyzed cascade difunctionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization was achieved and used to regiospecifically construct a variety of phosphorylated…
Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides.
TLDR
An efficient method for the synthesis of difluoroalkylated 2-azaspiro and saturated spirocyclohexanone scaffold via copper-catalyzed difleudoalkylation of N-benzylacrylamides with ethyl bromodifluorosoroacetate has been established.
Copper‐Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl‐Substituted Spiro[indole‐3,3′‐pyrrolidine] Derivatives
A copper-catalyzed cascade reaction involving trifluoromethylation of acrylamides coupled with ring closure and indole dearomatization is reported. This facile transformation was highly…
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A simple base and ligand free copper catalyzed method for the construction of trifluoromethylated benzoxazines has been developed by using Umemoto's reagent. It involves the oxidative…
Visible light-induced intramolecular dearomative cyclization of α-bromo-N-benzyl-alkylamides: efficient construction of 2-azaspiro[4.5]decanes.
An efficient intramolecular dearomative cyclization via visible light-induced photoredox catalysis allows for a highly regioselective dearomative cyclization of α-bromo-N-benzyl-alkylamides to…
Palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides: facile access to azaspirocyclohexadienones.
TLDR
An efficient palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides with β-bromoalkyl esters and ketones reacted smoothly to provide important azaspirocyclohexadienones in moderate to excellent yields.
Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center.
A Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved…
Iron-catalyzed cascade cyanoalkylation/radical dearomatization of N-phenylcinnamamides: access to cyanoalkylated 1-azaspiro[4.5]decanes
An iron-catalyzed cascade radical cyanoalkylative dearomatization of N-phenyl cinnamamides was developed. A direct access to the 1-azaspiro[4.5]decanes motif with good regioselectivity and…
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