Asymmetric 1,4-addition of organoboronic acids to alpha,beta-unsaturated ketones and 1,2-addition to aldehydes catalyzed by a palladium complex with a ferrocene-based phosphine ligand

作者：Suzuma Yoshinori; Hayashi Shoko; Yamamoto Tetsuya; Oe Yohei; Ohta Tetsuo^*; Ito Yoshihiko

来源：Tetrahedron: Asymmetry , 2009, 20(23): 2751-2758.

DOI：10.1016/j.tetasy.2009.11.025

A combination of palladium with ferrocene-based phosphine ligand with a carbon-bromine bond was found to be a good catalyst for the 1,4-addition of arylboronic acids to alpha,beta-unsaturated ketones and the 1,2-addition to aldehydes. Using Pd(dba)(2) and (S,R-p)-[ 1-(2-bromoferrocenyl)ethyl]diphenylphosphine (S,R-p)-1, 3-phenylcyclohexanone was obtained from the reaction of 2-cyclohexen-1-one with phenylbotonic acid in the presence of K2CO3 in toluene at room temperature after 3 h in 92% yield with 76% ee. In the 1,2-addition of 4-methylphenylboronic acid to benzaldehyde, 96% of (4-methylphenyl)phenylmethanol was afforded after 24 h, while the enantiomeric excess was only 6%.

• 出版日期2009-12-11