Abstract

Oxazolidinethiones and thiazolidinethiones constitute a class of versatile chiral auxiliaries for asymmetric synthesis. Their easy preparation from readily available β-amino-alcohols and the high levels of asymmetric induction they provide make them excellent chiral auxiliaries useful for the preparation of chiral intermediates in the synthesis of natural products. These chiral auxiliaries have been utilized in a wide variety of synthetic transformations such as asymmetric aldol condensation, stereoselective alkylation of different electrophiles, stereoselective differentiation of enantiotopic groups in molecules bearing prochiral centers, and other interesting applications. This review attempts to summarize the preparation, synthetic applications, and cleavage of oxazolidinethiones and thiazolidinethiones, as well as the manipulation of chiral intermediates obtained in asymmetric transformations involving these chiral auxiliaries.

Keywords: asymmetric synthesis, oxazolidinethiones, thiazolidinethiones, asymmetric aldol additions, retronecine, discodermolide, salinomycin, altohyrtin, pateamine, decarestrictine, mycothiazole