Palladium-Catalyzed Insertion of α-Diazoesters into Vinyl Halides To Generate α,β-Unsaturated γ-Amino Esters

As easy as 1, 2, 3: A palladium-catalyzed three-component coupling generates α,β-unsaturated γ-amino acids in a single step (see scheme). The reaction is believed to involve migration of a vinyl substituent to a highly electrophilic palladium carbene. Unlike previous synthetic approaches, this synth...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (20), p.3677-3680
Main Authors: Kudirka, Romas, Devine, Sean K.J, Adams, Christopher S, Van Vranken, David L
Format: Article
Language:English
Subjects:
amino acids
CC coupling
diazo compounds
palladium
peptide mimics
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Summary:As easy as 1, 2, 3: A palladium-catalyzed three-component coupling generates α,β-unsaturated γ-amino acids in a single step (see scheme). The reaction is believed to involve migration of a vinyl substituent to a highly electrophilic palladium carbene. Unlike previous synthetic approaches, this synthesis provides access to γ-amino acids with non-natural side chains.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200805483