Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols. Issue 25 (12th March 2018)

• Record Type: Journal Article
• Authors: Niemi, Teemu; Fernández, Israel; Steadman, Bethany; Mannisto, Jere K.; Repo, Timo
• Is Part Of: Chemical communications. Volume 54:Issue 25(2018)
• Page Start: 3166
• Page End: 3169
• Publication Date: 2018-03-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc00636a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Selective, straightforward, and efficient synthesis of cyclic carbamates from CO2 and amino alcohols. 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 SN 2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.