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Although the wide variety of heterocyclic compounds is common knowledge, chiral 2-oxazolidinones are recognized as some of the most important heterocycles in medicinal chemistry. Many important pharmaceutical molecules have been constructed based on the chiral 2-oxazolidinone backbone. Therefore, the development of even more efficient catalytic methods for the synthesis of chiral 2-oxazolidinones remains a very important pursuit in the field of synthetic organic chemistry. This review summarizes the coupling reactions of epoxides and isocyanates for the preparation of 2-oxazolidinones. Both metal catalysts and organocatalysts promote these reactions. Optically pure 2-oxazolidinones are prepared from optically pure epoxide substrates via these catalytic methods. A synthetic example of a commercially available pharmaceutical compound utilizing this method is also introduced. © 2022 Wiley Periodicals LLC.


Ken Okuno, Ryuichi Nishiyori, Koki Abe, Taiki Mori, Seiji Shirakawa. Efficient methods for the synthesis of chiral 2-oxazolidinones as pharmaceutical building blocks. Chirality. 2022 Jul;34(7):915-924

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PMID: 35488466

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