A Chiral Bidentate sp2-N Ligand, Naph-diPIM: Application to CpRu-Catalyzed Asymmetric Dehydrative C-, N-, and O-Allylation

Papers published
Kengo Miyata, Hironori Kutsuna, Sho Kawakami, and Masato Kitamura Angew. Chem. Int. Ed., 2011, 50, 4649–4653. DOI:10.1002/anie.201100772
  • Geuther-Wislicenus alkylation of 1,3-dicarbonyl compounds has been one of the most frequently utilized C–C bond formations in organic synthesis since the discovery in 1863. Tsuji revolutionized this chemistry to the Pd-catalyzed allylation in 1965, and then Trost reported the first asymmetric version in 1977. The reports have spurred the subsequent research on the related chemistry, which mainly utilizes various chiral phosphine–Pd complexes and others including Mo, Ir, Ru, and Rh complexes. Coupled with the high synthetic utility of "allyl group," the asymmetric Tsuji-Trost reaction has realized the synthesis of various natural products. However, stoichiometric amount of base is required for generation of the metal enolate, and allylic alcohols must be activated as the halides or the esters. The direct dehydrative route using allylic alcohol itself has been realized, for the first time, by use of a redox-mediated donor-acceptor bifunctional catalyst, CpRu–Naph-diPIM-dioxo-R/pTsOH.

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