Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5221680 | Tetrahedron | 2011 | 6 Pages |
Abstract
The first (organo)catalytic method for regio- and chemoselective aza-Friedel-Crafts (FC) alkylation of indoles and pyrroles with commercially available methyl α-acetamidoacrylates has been discovered. It minimizes/eliminates common competing reactions that occur due to the high and multiatom-nucleophilic character of indole and pyrrole. Diverse quaternary α-amino acids were successfully prepared in good yield and high selectivity using low catalyst loading. The enantioselective variant using BINOL-derived phosphoric acids was also explored with indole providing the desired F-C alkylation product with moderate enantioselectivities.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Marika Righi, Francesca Bartoccini, Simone Lucarini, Giovanni Piersanti,