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Issue 43, 2020
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Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides

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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.

Graphical abstract: Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides

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Article information


Submitted
06 Apr 2020
Accepted
20 Apr 2020
First published
20 Apr 2020

Chem. Commun., 2020,56, 5823-5826
Article type
Communication

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

M. Velázquez, S. Alberca, J. Iglesias-Sigüenza, R. Fernández, J. M. Lassaletta and D. Monge, Chem. Commun., 2020, 56, 5823
DOI: 10.1039/D0CC02478C

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