Syntheses and reactions of optically active alpha-aminoallenylstannanes.
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.
Ranslow
Peter B D
PB
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Hegedus
Louis S
LS
de los Rios
Cristobal
C
D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D017971:Tin Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D017971:Tin Compounds; C031525:stannane