Enantioselective Catalytic Allylation of Carbonyl Groups by Umpolung of π-Allyl Palladium Complexes

Diethylzinc mediates the asymmetric allylation of aldehydes through Umpolung of a π‐allyl palladium complex. An investigation of the palladium source and the chiral monophosphane ligands have shown that the leaving group has a dramatic effect on the enantioselectivity of the reaction. The procedure...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-02, Vol.43 (7), p.846-849
Main Authors: Zanoni, Giuseppe, Gladiali, Serafino, Marchetti, Alberto, Piccinini, Paolo, Tredici, Ilenia, Vidari, Giovanni
Format: Article
Language:English
Subjects:
Acetates - chemistry
Aldehydes - chemistry
Allyl Compounds - chemistry
allylation
asymmetric synthesis
Benzaldehydes - chemistry
Catalysis
Chemical Phenomena
Chemistry, Organic
Chemistry, Physical
Cyclohexanes - chemistry
Electrons
enantioselectivity
Ketones - chemistry
ligand design
Ligands
Molecular Structure
Organic Chemistry Phenomena
Palladium - chemistry
Phosphines - chemistry
Propanols - chemistry
Stereoisomerism
Umpolung
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Summary:Diethylzinc mediates the asymmetric allylation of aldehydes through Umpolung of a π‐allyl palladium complex. An investigation of the palladium source and the chiral monophosphane ligands have shown that the leaving group has a dramatic effect on the enantioselectivity of the reaction. The procedure furnished products in satisfactory yields and up to 70 % ee (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352743