Metal-Controlled, Regioselective, Direct Intermolecular α- or γ-Amination with Azodicarboxylates

Organic Letters
Xin FuShu-Yu Zhang

Abstract

A metal-controlled, regioselective intermolecular amination of unsaturated N-acylpyrazoles with azodicarboxylates is described. Under zinc catalysis, the N-acylpyrazole substrates undergo amination at the α-position of the N-acylpyrazole moiety. Conversely, with silver as the catalyst, the reaction gave γ-amination products. Both catalytic protocols provided alternative, convenient, and simple strategies for efficiently and regioselectively accessing structurally unique C-N-bond containing compounds. The synthetic utility of this method was illustrated by a gram-scale experiment and subsequent efficient synthesis of the γ-amino acid analogue.

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Citations

Jul 10, 2019·Chemical Society Reviews·Carmen NájeraMiguel Yus
Dec 19, 2019·Chemical Communications : Chem Comm·Jian LeiXiaolan Xie

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