STEREOCONTROLLED SYNTHESIS VIA CHIRAL AZIRIDINES

The use of chiral, non-racemic, aziridines for stereochemical control in diastereo- and enantioselective synthesis is described. Such aziridines are readily available in quantity from the corresponding chiral epoxides, and can be utilised: (i) as chiral substrates, e.g. for the enantioselective synthesis of carbapenem antibiotics and non-proteinogenic amino acids; (ii) as efficient chiral auxiliaries for diastereoselective enolate alkylation and aldol reactions; (iii) as chiral ligands, e.g. for enantioselective OsO4-mediated 1,2-dihydroxylation of olefins.