title: Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: application of an organocatalytic direct vinylogous aldol reaction.
abstract: The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.
authors.affiliation: Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada, A1B 3X7. spansare@mun.ca
authors.forename: Sunil V
authors.initials: SV
authors.lastname: Pansare
authors.forename: Eldho K
authors.initials: EK
authors.lastname: Paul
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C529304:3-hydroxypipecolic acid; D000447:Aldehydes; D010875:Pipecolic Acids; D010880:Piperidines; C080755:3-(2-methoxybenzylamino)-2-phenylpiperidine; C103788:3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine; C116609:3-hydroxybutanal