A Fascination with 1,2-Diacetals

1,2-Diacetals are readily prepared, rigid structural motifs that provide a wide range of opportunities for applications in natural product assembly. These uses encompass selective 1,2-diol or α-hydroxy acid protection, enantiotopic recognition and desymmetrization methods, chiral memory applications, and reactivity control in oligosaccharide synthesis, as well as functioning as templating components, chiral auxiliaries, and building blocks. 1,2-Diacetals are often more stable and lead to products with enhanced crystallinity compared to their five-ring acetonide counterparts. Many 1,2-diacetals have favorable NMR parameters, which facilitate structural assignment, particularly during asymmetric reaction processes.