Fine-Tuning Monophosphine Ligands for Enhanced Enantioselectivity. Influence of Chiral Hemilabile Pendant Groups

C 2 -Symmetric P-(2-X-aryl)-2,5-dialkylphospholanes (X = dioxolan-2-yl or dioxan-2-yl), designed on the basis of a working model for asymmetric induction, are effective ligands for the Ni(II)-catalyzed asymmetric hydrovinylation of styrenes. Excellent yields (>99%), selectivities for the desired...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 9; pp. 1515 - 1517
Main Authors Zhang, Aibin, RajanBabu, T. V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.04.2004
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Ligands
Molecular Conformation
Nickel - chemistry
Phosphines - chemical synthesis
Phosphines - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Styrenes - chemical synthesis
ASYMMETRIC CATALYSIS
HYDROVINYLATION REACTIONS
HYDROGENATION
CONJUGATE ADDITION
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Summary:C 2 -Symmetric P-(2-X-aryl)-2,5-dialkylphospholanes (X = dioxolan-2-yl or dioxan-2-yl), designed on the basis of a working model for asymmetric induction, are effective ligands for the Ni(II)-catalyzed asymmetric hydrovinylation of styrenes. Excellent yields (>99%), selectivities for the desired 3-arylbutenes (>99%), high S/C ratios (>1200), and ee's (up to 91%) have been realized for a number of prototypical vinylarenes. In the dioxolane series, the selectivity depends on the configuration of the C4 and C 5 carbons.
Bibliography:Medline
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0495063