Issue 25, 2018

Carbon dioxide-based facile synthesis of cyclic carbamates from 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 SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

Graphical abstract: Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

Supplementary files

Article information

Article type
Communication
Submitted
25 Jan 2018
Accepted
05 Mar 2018
First published
05 Mar 2018
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2018,54, 3166-3169

Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

T. Niemi, I. Fernández, B. Steadman, J. K. Mannisto and T. Repo, Chem. Commun., 2018, 54, 3166 DOI: 10.1039/C8CC00636A

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