1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architecturesElectronic supplementary information (ESI) available. See DOI: 10.1039/c4ob01920b

A diversity of new functionalized acyclic chiral pyrroloamide compounds were synthesized by a simple and robust process involving the creation of a C-C bond between unprotected pyrroles and acyclic chiral acrylamides using Lewis acids. This alkylation reaction using Michael acceptors has been optimized, allowing us to obtain channel selective access to monoalkylated or dialkylated pyrroles, in good yields. Di- and tripeptide deriving acrylamides have also been used as the reaction partner. A variety of new chiral functionalized pyrroloamides have been synthesized by a simple and robust process involving Lewis acids. Unprotected pyrrole could be selectively monoalkylated or dialkylated.