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Palladium‐Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N ‐Acyloxazolinones as Ester Enolate Equivalents
Author(s) -
Trost Barry M.,
Michaelis David J.,
Charpentier Julie,
Xu Jiayi
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105801
Subject(s) - enol , palladium , alkylation , tsuji–trost reaction , catalysis , chemistry , organic chemistry , allylic rearrangement , carboxylic acid , medicinal chemistry , imide
Triple A : A general asymmetric allylic alkylation of ester enolate equivalents at the carboxylic acid oxidation state is reported. N ‐Acylbenzoxazolinone‐derived enol carbonates were synthesized and employed in the palladium‐catalyzed alkylation reaction. The imide products were readily converted into a series of carboxylic acid derivatives without loss of enantiopurity.