Beilstein J. Org. Chem.2005,1, No. 13, doi:10.1186/1860-5397-1-13
rearrangement (S)-2(methoxymethyl)pyrrolidine 22 was then explored as the chiralauxiliary.[25] This auxiliary was selected to include a co-ordinating oxygen in place of the bulky diphenylmethane group in 14 to compare steric versus co-ordination effects. Allylation then gave 23 as the required aza-Claisen
Beilstein J. Org. Chem.2005,1, No. 2, doi:10.1186/1860-5397-1-2
chiralauxiliary. The source of the asymmetry means that the approach would be amenable to the synthesis of the enantiomeric aza-C-linked disaccharide derivatives. A key feature of the approach was the potential to switch between one- and two-directional synthetic steps, allowing the selective