Palladium‐Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives:  N ‐Acyloxazolinones as Ester Enolate Equivalents | Zendy

Trost Barry M. | Zendy; Michaelis David J. | Zendy; Charpentier Julie | Zendy; Xu Jiayi | Zendy

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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.

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