Diastereoselective Room-Temperature Pd-Catalyzed α-Arylation and Vinylation of Arylmandelic Acid Derivatives

Palladium-catalyzed α-arylation and vinylation of dioxolane (S,S)-I, easily obtained from (S)-mandelic acid, proceeds with high yields and excellent diastereoselectivity at room temperature employing commercially available P(t-Bu)3·HBF4 and Pd(OAc)2 as a catalytic precursor system. This method displ...

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Bibliographic Details
Published in:Organic letters 2009-04, Vol.11 (7), p.1543-1546
Main Authors: Jiang, Lei, Weist, Stefan, Jansat, Susanna
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Dioxolanes - chemical synthesis
Dioxolanes - chemistry
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Mandelic Acids - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
Temperature
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Summary:Palladium-catalyzed α-arylation and vinylation of dioxolane (S,S)-I, easily obtained from (S)-mandelic acid, proceeds with high yields and excellent diastereoselectivity at room temperature employing commercially available P(t-Bu)3·HBF4 and Pd(OAc)2 as a catalytic precursor system. This method displays general utility for a large variety of aryl, heteroaryl, and vinyl bromides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900131q