title: Stereocontrolled synthesis of psi[CH = CH] dipeptide isosteres.
abstract: A new stereocontrolled synthesis of the psi[CH = CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific alpha-alkylation of delta-amino-gamma-mesyloxy-alpha,beta-unsaturated esters. The broad availability of nucleophilic alpha-side chains by this method allows the preparation of a wide variety of psi[CH = CH] isosteres with predictable stereochemistry.
authors.affiliation: Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, IL.
authors.forename: D J
authors.initials: DJ
authors.lastname: Kempf
authors.forename: X C
authors.initials: XC
authors.lastname: Wang
authors.forename: S G
authors.initials: SG
authors.lastname: Spanton
mesh_terms: D000478:Alkylation; D004151:Dipeptides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D004151:Dipeptides; D004952:Esters