Asymmetric Synthesis of Alkyl Aziridine- 2-Carboxylates from Chiral 3'-Benzyloxy-aminoimides

摘要

The use of aziridinecarboxylates as intermediates in the synthesis of optically active compounds is a subject of current interest. The ring-opening of aziridines, a consequence of ring strain, is the most important feature of their chemistry and serves as the basis of the synthesis of substituted α- and β-amino acids, which is a topic of interest in our laboratory. Enantiomerically pure aziridines are available not only by separation of racemic mixtures, successfully performed by enzymatic resolution, but can also be prepared starting from β-hydroxy α-amino acids such as serine or threonine. Recently Zwanenburg and co-workers reported an interesting synthesis of aziridine-2-carboxylates from the corresponding chiral oxi-ranes. Furthermore, convenient methods have been reported for the synthesis of this class of compounds from α, β-unsaturated chiral imides relying on the reaction of 2,3-dihalocarboxylic acid derivatives with primary amines or ammonia.