title: Syntheses and reactions of optically active alpha-aminoallenylstannanes.
abstract: Lithiation/stannylation of optically active N-propargyloxazolidinones produced optically active alpha-oxazolidinonylallenylstannanes. Reaction of these with aldehydes in the presence of BF(3).OEt(2) produced beta-hydroxypropargylamines with high syn diastereoselectivity and ee. These were converted to gamma-hydroxy-beta-amino acids by oxidative cleavage of the alkyne.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Peter B D
authors.initials: PB
authors.lastname: Ranslow
authors.forename: Louis S
authors.initials: LS
authors.lastname: Hegedus
authors.forename: Cristobal
authors.initials: C
authors.lastname: de los Rios
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D017971:Tin Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D017971:Tin Compounds; C031525:stannane