Preparation of Aminosaccharides Using Ester-Imine Condensations: Syntheses of Methyl N-Benzoylacosaminide and Methyl N-(Oxo(phenylmethoxy)acetyl)daunosaminide from (S)-Ethyl 3-Hydroxybutyrate

Article abstract of DOI:10.1016/0040-4020(89)80126-7

The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl imine 2 to afford β-lactam 4.The same dianion reacted with N-aryl imine 10 to give β-lactams 11, 12, and 13.A three-step sequence was used to convert 4 into the β-lactam-pyra