Niemi Teemu, Fernández Israel, Steadman Bethany, Mannisto Jere K, Repo Timo
Department of Chemistry, University of Helsinki, P.O. Box 55, 00014, Finland.
Departamento de Quimica Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain.
Chem Commun (Camb). 2018 Mar 28;54(25):3166-3169. doi: 10.1039/c8cc00636a. Epub 2018 Mar 12.
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 S2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.
我们在此报告了一种直接通用的方法，可在外部碱和羟基活化试剂存在的情况下，由氨基醇和二氧化碳合成环状氨基甲酸酯。利用对甲苯磺酰氯（TsCl），该反应在温和条件下进行，并且该方法完全适用于制备各种高附加值的五元环和六元环以及双环稠合环氨基甲酸酯。密度泛函理论（DFT）计算和实验结果表明该反应具有S2型反应机理，具有高区域选择性、化学选择性和立体选择性。
