Selective Cross-Dimerization’s of conjugated Compounds by Ru(0) Catalyst

Date & time

11am–12pm 13 August 2014


Building 138, Seminar Room


Prof Masafumi Hirano


 Gavin Perri

One of the ultimate goals for the synthetic chemistry is the enantioselective synthesis by a zero-emission process. In this presentation, we disclose how we develop the first enatioselective cross-dimerization between substituted alkenes. A Ru (0) complex having a chiral diene ligand2-methylbicycle[3.3.1]nona-2,6-diene (S,S)-1b was newly prepared. The treatment of methyl methacrylate with 2,5-dihydrofurane in the presence of (S,S)-1b (10 mol%) at 20°C for 7 days produced 4b in 74% yield and 80% ee.1 This reaction goes through the oxidative coupling mechanism.
(1) Hiroi, Y.; Komine, N.; Komiya, S.; Hirano, M. Org. Lett. 2013, 15, 2486.
(2) Hirano, M.; Inoue, H.; Okamoto, T.; Ueda, T.; Komine, N.; Komiya, S.; Wang, X.-Q.; Bennett, M. A. New J.
Chem. 2013, 37, 3433.

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