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

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 as...

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Bibliographic Details
Published in:Organic letters 2002-08, Vol.4 (16), p.2799-2801
Main Authors: Shimada, Toyoshi, Kina, Asato, Ikeda, Syushiro, Hayashi, Tamio
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol026376u