A novel synthesis of hydroxyglycine retropeptidic derivatives was achieved through a Passerini 3-component reaction of glyoxyl amides or esters, followed by an unprecedented environmentally benign zinc catalysed solvolysis.
The first allylic amination of Passerini acetates is described, where both a and g-substitution products are obtained regioselectively from chromone derived adducts. While a-substitution occurs in THF, CuCl in methanol catalyses a tandem amination followed by a rearrangement leading to g-amino acid-derived chromones.
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