Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to [alpha],[alpha]-Disubstituted [alpha]-Amino Acids

An unprecedented enantioselective allylic alkylation of readily available aldimine esters has been developed, and is catalyzed by a synergistic Cu/Pd catalyst system. This strategy provides facile access to nonproteinogenic [alpha],[alpha]-disubstituted [alpha]-amino acids in high yield with excelle...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-09, Vol.56 (40), p.12312
Main Authors: Wei, Liang, Xu, Shi-Ming, Zhu, Qiao, Che, Chao, Wang, Chun-Jiang
Format: Article
Language:English
Subjects:
Alkylation
Amino acids
Catalysis
Chemical industry
Enantiomers
Esters
Palladium
Peptidomimetics
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Summary:An unprecedented enantioselective allylic alkylation of readily available aldimine esters has been developed, and is catalyzed by a synergistic Cu/Pd catalyst system. This strategy provides facile access to nonproteinogenic [alpha],[alpha]-disubstituted [alpha]-amino acids in high yield with excellent enantioselectivity. The more challenging double allylic alkylation of glycinate-derived imine esters was also realized. Furthermore, this methodology was applied for the construction of the key intermediate of PLG peptidomimetics.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201707019