title: Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process.
abstract: Herein, we report an unprecedented, short and diastereo-selective synthesis of newly reported aza-diketopiperazine (aza-DKP) scaffolds starting from amino acids. The strategy is based on a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation of allyl-substituted aza-DKP, followed by a diastereoselective functionalization of the platform. This methodology allows the synthesis of novel bicyclic and tricyclic aza-DKP scaffolds incorporating six- or seven-membered rings, with potential applications in medicinal chemistry.
authors.affiliation: Laboratoire d'Innovation Thérapeutique, UMR7200 CNRS/Université de Strasbourg, Labex Médalis, Faculté de Pharmacie, 74 route du Rhin, 67412 Illkirch, France. nicolas.girard@unistra.fr dominique.bonnet@unistra.fr.
authors.forename: Pierre
authors.initials: P
authors.lastname: Regenass
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Margathe
authors.forename: André
authors.initials: A
authors.lastname: Mann
authors.forename: Jean
authors.initials: J
authors.lastname: Suffert
authors.forename: Marcel
authors.initials: M
authors.lastname: Hibert
authors.forename: Nicolas
authors.initials: N
authors.lastname: Girard
authors.forename: Dominique
authors.initials: D
authors.lastname: Bonnet
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001372:Aza Compounds; D054659:Diketopiperazines; D012238:Rhodium