Cobalt(diamine)-catalyzed cross-coupling reaction of alkyl halides with arylmagnesium reagents: stereoselective constructions of arylated asymmetric carbons and application to total synthesis of AH13205.
A cobalt-diamine complex catalyzes the cross-coupling reactions of primary and secondary alkyl halides with aryl Grignard reagents. It is confirmed that oxidative addition of alkyl halide to cobalt proceeds via a radical process. Optically pure Ueno-Stork halo acetals undergo diastereoselective cross-coupling reactions, the products of which are transformed into optically active THF derivatives. A sequential radical cyclization/arylation reaction under cobalt catalysis provides extremely short access to a synthetic prostaglandin AH13205.
Ohmiya
Hirohisa
H
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Yorimitsu
Hideki
H
Oshima
Koichiro
K
D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011466:Prostanoic Acids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D011466:Prostanoic Acids; C081039:AH 13205; D003035:Cobalt; D008274:Magnesium