Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols
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...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2018-03, Vol.54 (25), p.3166-3169 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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 S
N
2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.
Selective, straightforward, and efficient synthesis of cyclic carbamates from CO
2
and amino alcohols. |
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ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/c8cc00636a |