Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols.
Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent delta-elimination of Rh(i)-OH.
Miura
Tomoya
T
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. murakami@sbchem.kyoto-u.ac.
Shimizu
Hiroshi
H
Igarashi
Tomohiro
T
Murakami
Masahiro
M
D000438:Alcohols / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D000466:Alkadienes; D001897:Boronic Acids; D009942:Organometallic Compounds; D013267:Stilbenes; D012238:Rhodium