As a versatile and sustainable C1 source, carbon dioxide can substitute toxic reagents such as isocyanates and phosgene in many organic syntheses. In particular, it readily couples with amines to give various carbamate species. This reactivity can be exploited further in the synthesis of cyclic carbamates, which are structural motifs found in many antibiotics and other pharmaceutically relevant or otherwise high value-added compounds. We have recently reported straightforward and general methods for the synthesis of cyclic carbamates.<sup>1-3</sup> For example, utilizing p-toluenesulfonyl chloride (TsCl), various amino alcohols react with carbon dioxide 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 an SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.<br/><br/>

Carbon dioxide as a building block for synthesis of cyclic carbamates

2019 Spring National Meeting

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