A Novel Axially Chiral 2,2‘-Bipyridine <i>N,N</i><i>‘</i>-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.