title: Diastereofacial solid phase synthesis and self-promoted cleavage of a [2.2.1] bicyclic diversity scaffold.
abstract: [reaction: see text]. We have previously described a diastereofacially selective 1,3-dipolar cycloaddition reaction of isomünchnones with vinyl ethers. While adapting this methodology for solid phase synthesis, we discovered a chemoselective and self-promoted linker aminolysis that provides liberated product in high purity, at a significantly enhanced rate. Herein we describe the implementation of a chiral auxiliary as a solid-phase linker, the detailed investigation of its unique aminolysis, and the utility of this cleavage within a chemical diversity format.
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06511, USA.
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Savinov
authors.forename: David J
authors.initials: DJ
authors.lastname: Austin
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012211:Rhenium; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001643:Bridged Bicyclo Compounds; D012211:Rhenium