Polymer-Supported Pyridine−Bis(oxazoline). Application to Ytterbium-Catalyzed Silylcyanation of Benzaldehyde

Terminal acetylenes containing hydroxy and carboxylic acid groups were subjected to Sonogashira coupling with 4-bromo-2,6-bis[(R)-4-phenyloxazolin-2-yl]pyridine and the resulting pybox derivatives were immobilized on Tentagel resins. Ytterbium(III) chloride complexes of the polymeric ligands catalyz...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 20; pp. 3663 - 3665
Main Authors Lundgren, Stina, Lutsenko, Serghey, Jönsson, Christina, Moberg, Christina
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Kemi
NATURAL SCIENCES
NATURVETENSKAP
Organic chemistry
Organisk kemi
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
LIGANDS
COMPLEXES
polymer
pyridine derivative
benzaldehyde
oxazoline derivative
ytterbium
silylation
chemical reaction
reaction analysis
asymmetric catalysis
addition reaction
article
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Summary:Terminal acetylenes containing hydroxy and carboxylic acid groups were subjected to Sonogashira coupling with 4-bromo-2,6-bis[(R)-4-phenyloxazolin-2-yl]pyridine and the resulting pybox derivatives were immobilized on Tentagel resins. Ytterbium(III) chloride complexes of the polymeric ligands catalyzed the addition of trimethylsilyl cyanide to benzaldehyde with 80−81% ee. The ligands were reused more than 30 times without any loss in selectivity or activity, and the metal complexes could be recovered and reused at least four times, although with slightly decreasing activity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol0353363