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Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides.

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Catalysts generated by combinations of Pd(TFA)2 and pyridine-hydrazone ligands have allowed the asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protected glyoxylate-derived hydrazones, yielding α-aryl α-hydrazino esters/amides… Click to show full abstract

Catalysts generated by combinations of Pd(TFA)2 and pyridine-hydrazone ligands have allowed the asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protected glyoxylate-derived hydrazones, yielding α-aryl α-hydrazino esters/amides in high enantioselectivities. Subsequent removal of the carbamoyl moiety affords key building blocks en route to hydrazinopeptides, N-aminopeptides and peptidomimetics thereof.

Keywords: catalytic enantioselective; aryl hydrazino; hydrazino esters; esters amides; aryl

Journal Title: Chemical communications
Year Published: 2020

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