Solvent-Free Non-Covalent Organocatalysis: Enantioselective Addition of Nitroalkanes to Alkylideneindolenines as a Flexible Gateway to Optically Active Tryptamine Derivatives

A catalytic asymmetric addition of nitroalkanes to alkylideneindolenines, generated in situ from arylsulfonylindoles, is presented. Despite the weakness of the non‐covalent H‐bond interactions between catalyst and substrates, the performance of the bifunctional organocatalyst used was found to be es...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2012-05, Vol.354 (7), p.1373-1380
Main Authors: Fochi, Mariafrancesca, Gramigna, Lucia, Mazzanti, Andrea, Duce, Sara, Fantini, Stefano, Palmieri, Alessandro, Petrini, Marino, Bernardi, Luca
Format: Article
Language:English
Subjects:
Accessibility
asymmetric synthesis
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
nitroalkanes
Organic chemistry
organocatalysis
Preparations and properties
solvent-free conditions
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
tryptamine
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Summary:A catalytic asymmetric addition of nitroalkanes to alkylideneindolenines, generated in situ from arylsulfonylindoles, is presented. Despite the weakness of the non‐covalent H‐bond interactions between catalyst and substrates, the performance of the bifunctional organocatalyst used was found to be essentially unaffected by the polarity of the reaction medium. Nitroalkanes, mostly used in nearly stoichiometric amounts, could thus function both as solvents and reagents, resulting in a truly solvent‐free reaction. The broad substrate scope shown by the present transformation allowed the preparation of some optically active tryptamine precursors that are not accessible through the previous catalytic asymmetric methods.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201100737