Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones.
[reaction: see text] A novel type of cascade ring expansion process has been developed by the palladium-catalyzed reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. The reaction proceeds in a stereospecific manner to produce (Z)-2-(3-aryl-1-propenyl)cyclopentanones. It has also been found that regioselective alpha-arylation of alkenyl cyclopentanones proceeds to afford the alpha-arylated cyclopentanones.
Yoshida
Masahiro
M
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Sugimoto
Kenji
K
Ihara
Masataka
M
D000440:Butanols / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000440:Butanols; D003517:Cyclopentanes; D006847:Hydrocarbons, Iodinated; C007201:cyclopentanone; D010165:Palladium