Nickel-catalyzed arylative ring-opening of 3-methylenecycloalkane-1,1-dicarboxylates.
An arylative ring-opening reaction of cyclic allylmalonates with arylzinc reagents under nickel catalysis has been developed. Upon the ring-opening sp(3)C-sp(3)C bond cleavage, the allylic moiety serves as an allylic electrophile to react with arylzinc reagents. Simultaneously, the malonate moiety is converted to the corresponding zinc enolate, which can react further with electrophiles. The overall process increases molecular complexity and diversity starting from readily available substrates and is useful in organic synthesis.
Sumida
Yuto
Y
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; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D003998:Dicarboxylic Acids; D009942:Organometallic Compounds; D009532:Nickel; D015032:Zinc