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Preparation of optically pure 1,2,5-triphenylphospholane. Use as ligand for enantioselective transition-metal catalysis.

✍ Scribed by Jean-Claude Fiaud; Jean-Yves Legros

Book ID: 104225829
Publisher: Elsevier Science
Year: 1991
Tongue: French
Weight: 193 KB
Volume: 32
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93435-x

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✦ Synopsis

Base-catalyzed isomerization of achiral (E,E)-l ,2,5-triphenylphospholane oxide leads to the racemic (E,Z)isomer. Resolution by Supercritical Fluid Chromatography (SFC) followed by reduction gives the two enantiomers.

The activity of this new ligand is tested in palladium-catalyzed coupling of cyclohex-2-enyl acetate with nucleophiles.

Monophosphine ligands have been less useful than chelating biphosphines in enantioselective transitionmetal catalysis.1 In palladium-catalyzed coupling of allyl acetates and phenylzinc chloride however,

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