ArticleThe Journal of organic chemistry2012
Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.
Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Cascade Grignard Addition: Propargyl Claisen Rearrangement for the Stereoselective Synthesis of α-Allene Quaternary Centers in Cyclohexanones.Organic letters · 2025Article
- Rapid Access to 2,2-Disubstituted Indolines via Dearomative Indolic-Claisen Rearrangement: Concise, Enantioselective Total Synthesis of (+)-Hinckdentine A.Journal of the American Chemical Society · 2023Article
- EnantioselectiveOrganic letters · 2021Article
- Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment.Organic letters · 2018Article
- Direct Access to Highly Functionalized Heterocycles through the Condensation of Cyclic Imines and α-Oxoesters.The Journal of organic chemistry · 2017Article
- Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids.Organic letters · 2017Article
- Metal-catalyzed cascade rearrangements of 3-alkynyl flavone ethers.Organic letters · 2013Article
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Authors and funding
5 authors.
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Abstract
In this Article, a strategy to obtain highly enantioselective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation.
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