Enantioselective Construction of Bridged Multicyclic Skeletons: Intermolecular [2+2+2] Cycloaddition/Intramolecular Diels–Alder Reaction Cascade


  • This work was supported partly by the Grants-in-Aid for Scientific Research (Nos. 20675002 and 20⋅8746) from MEXT (Japan). We thank Dr. Hidetomo Imase and Maho Takahashi (TUAT) for their preliminary experiments, Takasago Int. Co. for the gift of segphos, and Umicore for generous support in supplying a rhodium complex.


original image

Bridging a gap: A cationic rhodium(I)/ligand complex catalyzes the title reaction of alkynes and amide-linked 1,5-dienes, leading to bridged multicyclic compounds, with high chemo-, regio-, and enantioselectivity (see scheme; Bn=benzyl).