title: Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids.
abstract: Sequential aldol condensation of aldehydes with methyl ketones followed by transition metal-catalyzed addition reactions of arylboronic acids to form β-substituted ketones is described. By using the 1,1'-spirobiindane-7,7'-diol (SPINOL)-based phosphite, an asymmetric version of this type of sequential reaction, with up to 92% ee, was also realized. Our study provided an efficient method to access β-substituted ketones and might lead to the development of other sequential/tandem reactions with transition metal-catalyzed addition reactions as the key step.
authors.affiliation: Department of Chemistry, College of Staten Island, Staten Island, New York 10314, USA.
authors.forename: Yuan-Xi
authors.initials: YX
authors.lastname: Liao
authors.forename: Chun-Hui
authors.initials: CH
authors.lastname: Xing
authors.forename: Matthew
authors.initials: M
authors.lastname: Israel
authors.forename: Qiao-Sheng
authors.initials: QS
authors.lastname: Hu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D001897:Boronic Acids; D007659:Ketones; C116609:3-hydroxybutanal; D012238:Rhodium