Construction of Monocyclic Eight-Membered Rings: Intermolecular Rhodium(I)-Catalyzed [6+2] Cycloaddition of 4-Allenals with Alkynes


  • This work was financially supported by Grants-in-Aid for Young Scientist (B) (no. 20790002) and for Scientific Research (B) (no. 23390001) from the Japan Society for the Promotion of Science (JSPS) and also by a Grant-in-Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis (no. 23105501)” from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). Y.O. acknowledges the Akiyama Foundation for financial support. A.H. thanks the JSPS for providing a Research Fellowship for Young Scientists.


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Rounding up: A RhI-catalyzed intermolecular cycloaddition of 4-allenals with alkynes has been developed that provides various monocyclic eight-membered rings in good to high yields in a stereoselective manner (see scheme). In addition, the chirality of the starting allene is transferred in this reaction, thereby giving optically active monocyclic eight-membered ring compounds.