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Short Paper | Special issue | Vol 95, No. 2, 2017, pp.1211-1229
Published online, 6th February, 2017
DOI: 10.3987/COM-16-S(S)72
Diastereo- and Enantioselective Construction of 6,7-Dioxabicyclo[2.2.1]heptane Derivatives by a Dirhodium(II)-Catalyzed Intramolecular C–H Insertion Reaction

Taku Miyazawa, Kozue Imai, Motoki Ito, Koji Takeda, Masahiro Anada,* Shigeki Matsunaga, and Shunichi Hashimoto*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan


The first diastereo- and enantioselective construction of bridged bicyclic ring systems by an intramolecular C–H insertion reaction is described. With dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, the C–H insertion of α-alkyl-α-diazoesters containing an ethylene ketal moiety at the γ-position provided methyl 6,7-dioxabicyclo[2.2.1]heptane-3-carboxylate derivatives with up to 95% ee and perfect diastereoselectivity.