title: A novel axially chiral 2,2'-bipyridine N,N'-dioxide. Its preparation and use for asymmetric allylation of aldehydes with allyl(trichloro)silane as a highly efficient catalyst.
abstract: [reaction: see text] New axially chiral 2,2'-bipyridine N,N'-dioxides were obtained by a new method that does not involve any procedures for the separation of enantiomers. One of the dioxides, (R)-3,3'-bis(hydroxymethyl)-6,6'-diphenyl-2,2'-bipyridine N,N'-dioxide, exhibited extremely high catalytic activity for the asymmetric allylation of aldehydes with allyl(trichloro)silane. The allylation of aromatic aldehydes proceeded in the presence of 0.01 or 0.1 mol % of the dioxide catalyst to give the corresponding homoallyl alcohols of up to 98% ee.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Japan.
authors.forename: Toyoshi
authors.initials: T
authors.lastname: Shimada
authors.forename: Asato
authors.initials: A
authors.lastname: Kina
authors.forename: Syushiro
authors.initials: S
authors.lastname: Ikeda
authors.forename: Tamio
authors.initials: T
authors.lastname: Hayashi