title: Stereocontrolled synthesis and alkylation of cyclic beta-amino esters: asymmetric synthesis of a (-)-sparteine surrogate.
abstract: A convenient method for the stereoselective synthesis of cyclic beta-amino esters from an iodo alphabeta-unsaturated ester and alpha-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UK.
authors.forename: Jean-Paul R
authors.initials: JP
authors.lastname: Hermet
authors.forename: Aurélien
authors.initials: A
authors.lastname: Viterisi
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Wright
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: McGrath
authors.forename: Peter
authors.initials: P
authors.lastname: O'Brien
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.forename: John
authors.initials: J
authors.lastname: Gilday
mesh_terms: D000478:Alkylation; D018360:Crystallography, X-Ray; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D013034:Sparteine / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D013034:Sparteine