Die organokatalytische asymmetrische Prins‐Cyclisierung

Thef irst enantioselective Friedel-Crafts alkylation of indoles and pyrroles with 3-hydroxy-3-indolyloxindoles to access twon ovelt ypes of 3,3-diaryloxindoles catalyzed by chiral imidodiphosphoric acids hasb een reported. Ar ange of quaternary carbon centered 3,3-diaryloxindoles were synthesized in high yield (up to > 99%) with excellent enantioselectivity (up to 98% ee)a tl ow catalyst loadings (as low as 0.5 mol%). TheF riedel-Crafts reaction between indoles and 3-hydroxy-3-indolyloxindoles is amenable to gram scale syntheses.

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Chiral Imidodiphosphoric Acids‐Catalyzed Friedel–Crafts Reactions of Indoles/Pyrroles with 3‐Hydroxy‐indolyloxindoles: Enantioselective Synthesis of 3,3‐Diaryloxindoles

Zhuo

Song

et al. 2016

Adv Synth Catal

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Iron(III) Chloride‐Catalyzed Tandem Aza‐Prins/Friedel–Crafts Cyclization of 2‐Arylethyl‐2,3‐butadienyl Tosylamides and Aldehydes‐An Efficient Synthesis of Benzo[f]isoquinolines

Lin

Cheng

2016

Adv Synth Catal

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An efficient approach for the synthesis of 1,2,3,4,5,6‐hexahydrobenzo[f]isoquinolines via a tandem aza‐Prins/Friedel–Crafts cyclization from 2‐arylethyl‐2,3‐butadienyl tosylamides and aldehydes has been developed. This iron(III) chloride‐catalyzed cascade cyclization at the room temperature with different types of aldehydes, such as aromatic and heteroaromatic aldehydes, alkyl aldehydes, and α,β‐unsaturated aldehydes, affords the products in moderate to excellent yields (up to 97 %). In this reaction, chlorotrimethylsilane was applied to activate the aldehydes. The cheap catalyst, the mild reaction conditions, and the broad scope of the substrates make this method highly useful.magnified image

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Imidodiphosphoric Acids Catalysed Asymmetric Functionaliza‐tion with Thiols: Access to Oxindole Derived ɑ‐Chiral Thioethers

et al. 2021

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Chiral imidodiphosphoric acid-catalysed asymmetric functionalization of 3-hydroxy bisindoles was established. Sulfur-containing groups could be successfully introduced into isatin frameworks using commercially available thiols. The transformation was compatible with substrates bearing distinct substituents, both aromatic and aliphatic thiols were amenable to afford the desired products. A total of 41 reactions furnished various chiral 3thiooxindoles in 23%-99% yield, with 72%-99% enantioselectivity.

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Die organokatalytische asymmetrische Prins‐Cyclisierung

Cited by 47 publications

References 101 publications

Chiral Imidodiphosphoric Acids‐Catalyzed Friedel–Crafts Reactions of Indoles/Pyrroles with 3‐Hydroxy‐indolyloxindoles: Enantioselective Synthesis of 3,3‐Diaryloxindoles

Chiral Imidodiphosphoric Acids‐Catalyzed Friedel–Crafts Reactions of Indoles/Pyrroles with 3‐Hydroxy‐indolyloxindoles: Enantioselective Synthesis of 3,3‐Diaryloxindoles

Iron(III) Chloride‐Catalyzed Tandem Aza‐Prins/Friedel–Crafts Cyclization of 2‐Arylethyl‐2,3‐butadienyl Tosylamides and Aldehydes‐An Efficient Synthesis of Benzo[f]isoquinolines

Imidodiphosphoric Acids Catalysed Asymmetric Functionaliza‐tion with Thiols: Access to Oxindole Derived ɑ‐Chiral Thioethers

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