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. Author manuscript; available in PMC: 2009 Mar 18.
Published in final edited form as: Nature. 2008 Sep 18;455(7211):323–332. doi: 10.1038/nature07370

Figure 3. Enantioselective C(sp3)–C(sp3) cross-coupling toward fluvirucinine A1 (17).

Figure 3

Sequential asymmetric C(sp3)–C(sp3) Negishi cross-couplings of racemic allylic chlorides and alkylzinc reagents catalyzed by nickel/(S,S)-16 enabled the rapid formal synthesis of Fluvirucinine A1 with excellent enantio- and diastereoselectivity, highlighting a creative solution to remote stereochemical control in unfunctionalized systems.51 Glyme, 1,2-dimethoxyethane; DMF, N,N-dimethylformamide. (Reduced to 45%)