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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.


Alexander Gratais, Xavier Pannecoucke, Samir Bouzbouz. 1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures. Organic & biomolecular chemistry. 2015 Jan 28;13(4):1082-90

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PMID: 25414990

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