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

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

Chem Commun (Camb)

Departamento de Química Orgánica, Universidad de Sevilla and Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/Prof. García González, 1, 41012 Sevilla, Spain.

Published: May 2020

AI Article Synopsis

  • The combination of Pd(TFA) and pyridine-hydrazone ligands serves as effective catalysts for the asymmetric addition of aryl boronic acids to specific hydrazone compounds.
  • These reactions produce α-aryl α-hydrazino esters and amides with high levels of enantioselectivity.
  • After removing the carbamoyl group, this process yields important building blocks for developing hydrazinopeptides, N-aminopeptides, and similar compounds.

Article Abstract

Catalysts generated by combinations of Pd(TFA) 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.

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Source
http://dx.doi.org/10.1039/d0cc02478cDOI Listing

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