ArticleNature communications2020
Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 47 citations in OpenAlex.
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- Development and mechanistic studies of calcium-BINOL phosphate-catalyzed hydrocyanation of hydrazones.Beilstein journal of organic chemistry · 2025Article
- Enantioselective synthesis of chiral α,α-dialkyl indoles and related azoles by cobalt-catalyzed hydroalkylation and regioselectivity switch.Nature communications · 2024Article
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- Enantioselective synthesis of N-alkylindoles enabled by nickel-catalyzed C-C coupling.Nature communications · 2022Article
- Photoinduced, Copper-Catalyzed Enantioconvergent Alkylations of Anilines by Racemic Tertiary Electrophiles: Synthesis and Mechanism.Journal of the American Chemical Society · 2022Article
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4 authors at 1 institution in 1 country.
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Abstract
Catalytic asymmetric functionalization of the N-H groups of indoles and carbazoles constitutes an important but less developed class of reactions. Herein, we describe a propargylation protocol involving the use of a lithium SPINOL phosphate as the chiral catalyst and our recently developed C-alkynyl N,O-acetals as propargylating reagents. The direct asymmetric N-propargylation of indoles and carbazoles provides hitherto inaccessible N-functionalized products. Notably, the efficiency of the system allows reactions to be run at a very low catalyst loading (as low as 0.1 mol%). Mechanistic information about the titled reaction is also disclosed. This study represents an advance in the direct asymmetric functionalization of the N-H bonds of indoles and carbazoles, and additionally expands on the application of chiral alkali metal salts of chiral phosphoric acids in asymmetric catalysis.
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