Palladium-Catalyzed Allylic Alkylation of Carboxylic Acid Derivatives: N-Acyloxazolinones as Ester Enolate Equivalents


  • We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences (Grant GM33049), for their generous support of our programs. D.J.M. also thanks the National Institutes of Health for a postdoctoral fellowship (F32GM093467-01).


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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.