Rhodium-catalyzed Intramolecular Aziridination of 5-O-Sulfamoylbutenolides: Efficient Stereospecific Access to Aziridino-γ-Iactones, Starting Materials for the Synthesis of Complex α- or β-Amino Acids

摘要

We have previously demonstrated that 2,3-aziridino-γ-lactones 1 are versatile starting materials for the synthesis of complex amino acids. Depending on whether a hard or soft nucleophile is used to open the aziridine ring, either α-amino or β-amino acids, respectively, can be obtained in optically pure form. Examples of α-amino acids prepared in this fashion include dihydroxyglutamic acid (DHGA, 2) as well as (-)-polyoxamic acid 3. In the case of β-amino acids, we have recently reported the synthesis of APTO 4, the P-amino acid component of the marine cyclic peptides Microsclerodermins C and D.