Premium
Solvent‐Free Non‐Covalent Organocatalysis: Enantioselective Addition of Nitroalkanes to Alkylideneindolenines as a Flexible Gateway to Optically Active Tryptamine Derivatives
Author(s) -
Fochi Mariafrancesca,
Gramigna Lucia,
Mazzanti Andrea,
Duce Sara,
Fantini Stefano,
Palmieri Alessandro,
Petrini Marino,
Bernardi Luca
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100737
Subject(s) - chemistry , enantioselective synthesis , organocatalysis , bifunctional , covalent bond , combinatorial chemistry , catalysis , tryptamine , reagent , phosphonate , substrate (aquarium) , organic chemistry , geology , biochemistry , oceanography
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.