Abstract

Background: Chiral three-membered heterocycles occupy a special place in medicinal and pharmaceutical chemistry related to their diversity of biological activities due to the strain incorporated in their skeletons. This review covers developments reported in the last thirteen years in asymmetric epoxidation, aziridination, azirination and thiirination applied to the synthesis of biologically relevant or natural three-membered heterocycles.

Results: This short review includes 63 references dedicated to the synthesis of natural and/or biologically relevant three-membered heterocycles based on asymmetric epoxidation in a first section, aziridination in a second section, azirination in a third section and thiirination in a fourth section.

Conclusion: This review demonstrates that in the past thirteen years, a number of biologically relevant three-membered heterocycles, including chiral epoxides, aziridines, azirines, and even thiiranes, have been synthesized on the basis of asymmetric epoxidation, aziridination, azirination, and thiirination methodologies. The multipurpose synthetic applicability and biologically activity of three-membered heterocycles will facilitate the medicinal chemists to plan, design and implement new approaches towards the discovery of novel drugs.

Keywords: Chiral three-membered heterocycles, biological activity, epoxides, aziridines, azirines, thiiranes, asymmetric synthesis.

Graphical Abstract