Copper-catalyzed intermolecular asymmetric propargylic dearomatization of indoles.

@article{Shao2015CoppercatalyzedIA,
  title={Copper-catalyzed intermolecular asymmetric propargylic dearomatization of indoles.},
  author={W. L. Shao and He Li and Chuan Liu and Chenjiang Liu and Shu‐Li You},
  journal={Angewandte Chemie},
  year={2015},
  volume={54 26},
  pages={
          7684-7
        }
}
The first copper-catalyzed intermolecular dearomatization of indoles by an asymmetric propargylic substitution reaction was developed. This method provides a highly efficient synthesis of versatile furoindoline and pyrroloindoline derivatives containing a quaternary carbon stereogenic center and a terminal alkyne moiety with up to 86 % yield and 98 % ee. 
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109 Citations

109 Citations

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Copper-catalyzed intermolecular asymmetric propargylic dearomatization of phenol derivatives.
TLDR
A copper-catalyzed intermolecular asymmetric propargylic dearomatization of phenol derivatives has been realized, providing a variety of optically active cyclohexadienone derivatives with up to >99% ee.
Palladium-Catalyzed Intramolecular Dearomatization of Indoles via Decarboxylative Alkynyl Termination.
TLDR
A highly diastereoselective dearomatization of indoles via palladium-catalyzed decarboxylative alkynyl termination was developed, which led to operationally simple conditions, short time, and broad substrate scope.
Palladium(0)-Catalyzed Intermolecular Allylic Dearomatization of Indoles by a Formal [4+2] Cycloaddition Reaction.
TLDR
Bridged indoline derivatives were synthesized by an intermolecular Pd-catalyzed allylic dearomatization reaction of substituted indoles, providing bridged indolines in excellent enantioselectivity.
Chiral Phosphoric Acid Catalyzed Intramolecular Dearomative Michael Addition of Indoles to Enones.
TLDR
An enantioselective intramolecular dearomative Michael addition of indolyl enones is presented and various enantioenriched spiro-indolenines bearing a quaternary stereogenic center were obtained with good yields and enantiOSElectivity under mild reaction conditions.
Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate.
TLDR
The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand.
Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation.
TLDR
The first Pd-catalyzed allylic dearomatization of substituted indoles triggered by C-H bond activation is reported, providing a straightforward access to 3,3-disubstituted indolines.
Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates.
The first copper-catalyzed asymmetric decarboxylative [4 + 1] cycloaddition of propargylic carbamates and sulfur ylides was successfully developed. This strategy led to a series of chiral indolines…
Copper-Catalyzed Asymmetric Propargylation of Indolizines.
TLDR
The utilization of copper-catalyzed asymmetric propargylation to install a terminal alkyne handle on indolizine heterocycle is reported.
Efficient Synthesis of N-Alkylated 4-Pyridones by Copper-Catalyzed Intermolecular Asymmetric Propargylic Amination.
TLDR
Copper-catalyzed intermolecular asymmetric propargylic amination with 4-hydroxypyridines has been realized for the first time and can be easily transformed to the core structure of quinolizidine alkaloids.
Spirooxindole synthesis via palladium-catalyzed dearomative reductive-Heck reaction.
Palladium-catalyzed intramolecular dearomative reductive-Heck reaction of C2-substituted indoles is developed, which provides access to structurally diverse 3,2'-spiropyrrolidine oxindoles. By…
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