title: Highly stereoselective modifications of peptides via Pd-catalyzed allylic alkylation of internal peptide amide enolates.
abstract: Pd-catalyzed allylations are excellent tools for stereoselective peptide modifications, showing several advantages compared to normal alkylations. Reactions of internal peptide amide enolates with Pd-allyl complexes proceed not only with high yields of up to 86%, they show also high regio- and diastereoselectivities (88-99%), giving rise to the trans-configured products. Therefore, this protocol is a powerful synthetic tool for the synthesis of natural product and drug molecules.
authors.affiliation: Institute for Organic Chemistry, Saarland University, Saarbruecken, Germany. u.kazmaier@mx.uni-saarland.de
authors.forename: Swarup
authors.initials: S
authors.lastname: Datta
authors.forename: Anton
authors.initials: A
authors.lastname: Bayer
authors.forename: Uli
authors.initials: U
authors.lastname: Kazmaier
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000577:Amides; D010455:Peptides; D010165:Palladium