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Issue 25, 2018
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Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

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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

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Supplementary files

Article information


Submitted
25 Jan 2018
Accepted
05 Mar 2018
First published
05 Mar 2018

This article is Open Access

Chem. Commun., 2018,54, 3166-3169
Article type
Communication

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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