Kinetic Resolution of Diols and Pyridyl Alcohols by Cu(II)(borabox)-Catalyzed Acylation

Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoyla...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 9; pp. 1879 - 1882
Main Authors Mazet, Clément, Roseblade, Stephen, Köhler, Valentin, Pfaltz, Andreas
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.04.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
REAGENT
HYDROGENATION
1,2-DIOLS
HETEROCYCLES
CONTAINING LIGANDS
SUBSTRATE
COMPLEXES
OLEFINS
DERIVATIVES
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Summary:Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol060443t