We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.
Fields of Science
- 116 Chemical sciences
- CARBOXYLATIVE CYCLIZATION
Niemi, T. Y. M., Fernández, I., Steadman, B., Mannisto, J. K., & Repo, T. J. (2018). Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols. Chemical Communications, 54(25), 3166-3169. https://doi.org/10.1039/C8CC00636A