Abstract
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.
| Original language | English |
|---|---|
| Journal | Chemical Communications |
| Volume | 54 |
| Issue number | 25 |
| Pages (from-to) | 3166-3169 |
| Number of pages | 4 |
| ISSN | 1359-7345 |
| DOIs | |
| Publication status | Published - 28 Mar 2018 |
| MoE publication type | A1 Journal article-refereed |
Fields of Science
- 116 Chemical sciences
- ATMOSPHERIC-PRESSURE
- CARBOXYLATIVE CYCLIZATION
- CO2
- 2-OXAZOLIDINONES
- URETHANES
- CONVERSION
- FIXATION
- OXAZOLIDIN-2-ONES
- ORGANOCATALYST
- AZIRIDINES
Cite this
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