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Issue 20, 2014
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Nucleophilic addition to N-alkoxyamides

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An amide group is one of the most abundant functional groups in organic synthesis. However, nucleophilic addition to amide carbonyls has received less attention than their construction due to their high stability. In this Perspective, we describe our recent progress with N-alkoxyamides. Incorporation of an N-alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. The reaction can introduce two different nucleophiles in a one-pot process, giving a variety of substituted amines. When the Schwartz reagent was used in the first reduction step, high chemoselectivity was observed in the presence of sensitive functional groups such as esters, which resulted in the concise total synthesis of (±)-gephyrotoxin.

Graphical abstract: Nucleophilic addition to N-alkoxyamides

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Article information

19 Feb 2014
15 Mar 2014
First published
18 Mar 2014

Org. Biomol. Chem., 2014,12, 3147-3150
Article type

Nucleophilic addition to N-alkoxyamides

T. Sato and N. Chida, Org. Biomol. Chem., 2014, 12, 3147
DOI: 10.1039/C4OB00389F

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