Synthesis of Various Bridged Ring Systems via Rhodium-Catalyzed Bridged (3+2) Cycloadditions.

Org Lett

Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

Published: January 2022

Here, we describe the rhodium-catalyzed bridged (3+2) cycloaddition cascade reactions of -sulfonyl-1,2,3-triazoles, which allowed the efficient diastereoselective construction of various functionalized and synthetically challenging bridged ring systems. This simple, direct transformation had a broad substrate scope and excellent functional group tolerance. The highly strained polycyclic bicyclo[2.2.2]octa[]indole core of fruticosine was synthesized efficiently using this methodology.

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http://dx.doi.org/10.1021/acs.orglett.1c03837DOI Listing

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