Journal
ORGANIC LETTERS
Volume 22, Issue 18, Pages 7147-7151Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02484
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A highly efficient, TFAA-BF3 center dot OEt2 mediated multicomponent coupling of amino acid, TFAA, and aromatics provides a broad library of 2-trifluoromethyl equipped 2,5-disubstituted/2,4,5-trisubstituted oxazoles or N-(trifluoroacetyl)-beta-aminoalkyl ketones. This amino acid tetra-functionalization approach involves amidation (C-N), anhydride (C-O), Friedel-Crafts acylation (C-C), and Robinson-Gabriel annulation (C-O) followed by dehydrative aromatization. This reaction takes place under operationally simple, mild, and metal-free conditions using readily available amino acids and aromatic compounds.
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