4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis

Abstract

4-Oxoazetidine-2-carbaldehydes or 4-formyl-β-lactams can be considered both as protected α-amino aldehydes and masked β-amino acids. These bifunctional compounds exhibit a valuable dual reactivity, which has been utilized in a broad range of synthetic applications. The present review is a survey of the recent salient synthetic achievements exploiting 4-oxoazetidine-2-carbaldehydes, with particular emphasis on diastereoselective processes. The usefulness of these substrates for the preparation of substances of biological interest, including α-amino acids, β-amino acids, amino sugars, polycyclic-β-lactams, alkaloids, and complex natural products is presented.