Catalytic Asymmetric C−H Activation of Alkanes and Tetrahydrofuran
journal contributionposted on 17.03.2000 by Huw M. L. Davies, Tore Hansen, Melvyn Rowen Churchill
Any type of content formally published in an academic journal, usually following a peer-review process.
Rhodium carbenoids derived from methyl aryldiazoacetates are capable of effective catalytic asymmetric C−H activation of a range of alkanes and tetrahydrofuran by a C−H insertion mechanism. Dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4) catalyzed decomposition of methyl aryldiazoacetates in the presence of alkanes results in intermolecular C−H insertions with good control of regioselectivity, diastereoselectivity, and enantioselectivity. The carbenoids derived from methyl aryldiazoacetates are considerably more chemoselective than carbenoids derived from diazoacetates. They strongly favor C−H insertions into secondary and tertiary sites. Formation of side products due to carbene dimerization is not a major problem with rhodium carbenoids derived from aryldiazoacetates.