Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran

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)pro (Rh-2(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 aryldiazoacetates.