title: 1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures.
abstract: 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.
authors.affiliation: CNRS, INSA, Université de Rouen, COBRA UMR 6014, 76821 Mont Saint Aignan Cedex, France. samir.bouzbouz@univ-rouen.fr.
authors.forename: Alexander
authors.initials: A
authors.lastname: Gratais
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.forename: Samir
authors.initials: S
authors.lastname: Bouzbouz
mesh_terms: D000178:Acrylamides / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D058116:Lewis Acids / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000178:Acrylamides; D000596:Amino Acids; D058116:Lewis Acids; D010455:Peptides; D011758:Pyrroles