title: delta-Amino beta-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A.
abstract: [formula: see text] delta-Amino beta-keto esters 3 and 11 are designed polyfunctionalized chiral building blocks for alkaloid synthesis and are prepared in one step from the corresponding sulfinimine (N-sulfinyl imine). Concise highly enantioselective four-step syntheses of 2-phenylpiperidine (7) and SS20846A (14) from 3 and 11, respectively, are described.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
authors.forename: F A
authors.initials: FA
authors.lastname: Davis
authors.forename: B
authors.initials: B
authors.lastname: Chao
authors.forename: T
authors.initials: T
authors.lastname: Fang
authors.forename: J M
authors.initials: JM
authors.lastname: Szewczyk
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D004952:Esters; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C408865:2-phenylpiperidine; D000470:Alkaloids; D004952:Esters; D010880:Piperidines; C408864:SS 20846A