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Pd-catalyzed carbonylative α-arylation of azlactones: A formal four-component coupling route to α,α-disubstituted amino acids

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Abstract We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved… Click to show full abstract

Abstract We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved to be suitable substrates in this formal four-component approach, providing the desired products in good to high yields. Other amino acids, such as methionine, leucine and phenylalanine could be functionalized in a similar manner with this methodology. The possibility for isotope labeling (13C, 2H) was demonstrated, as well as chemoselective transformations of the tricarbonyl-containing molecules.

Keywords: amino acids; disubstituted amino; catalyzed carbonylative; carbonylative arylation; arylation azlactones; formal four

Journal Title: Journal of Catalysis
Year Published: 2018

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