Palladium-catalyzed construction of amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions

The palladium catalyzed regio- and diastereo-selective allylic alkylation of ( R)-2-acetoxy-4-aryl-3-butene with N-(diphenylmethylidene)glycinate and N-(diphenylmethylidene)alaninate occurred. The stereochemistry was controlled by the use of o-(diphenylphosphino)carboxylic acid, and produced new ami...

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Bibliographic Details
Published in:Tetrahedron letters 2005-09, Vol.46 (39), p.6663-6666
Main Authors: Ikeda, Daiji, Kawatsura, Motoi, Uenishi, Junichi
Format: Article
Language:English
Subjects:
Amino acids derivatives
Pd-catalyzed allylic alkylation
Regio- and diastereo-selectivity
Vicinal chiral carbon centers
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Summary:The palladium catalyzed regio- and diastereo-selective allylic alkylation of ( R)-2-acetoxy-4-aryl-3-butene with N-(diphenylmethylidene)glycinate and N-(diphenylmethylidene)alaninate occurred. The stereochemistry was controlled by the use of o-(diphenylphosphino)carboxylic acid, and produced new amino acid derivatives possessing vicinal chiral quaternary and tertiary carbon centers at the α and β positions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.07.139