Nucleophilic addition to N-alkoxyamides

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3147-3150
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number20
DOIs
Publication statusPublished - 2014 May 28

Fingerprint

Amides
amides
Functional groups
Synthetic Chemistry Techniques
Nucleophiles
Amines
nucleophiles
Esters
Nitrogen
synthesis
nitrogen atoms
reagents
esters
Atoms
amines
reactivity
Schwartz reagent
gephyrotoxin
alkoxyl radical

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Nucleophilic addition to N-alkoxyamides. / Satou, Takaaki; Chida, Noritaka.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 20, 28.05.2014, p. 3147-3150.

Research output: Contribution to journalArticle

@article{8a59becc9c3d4e189e0c59cf6908e94b,
title = "Nucleophilic addition to N-alkoxyamides",
abstract = "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.",
author = "Takaaki Satou and Noritaka Chida",
year = "2014",
month = "5",
day = "28",
doi = "10.1039/c4ob00389f",
language = "English",
volume = "12",
pages = "3147--3150",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "20",

}

TY - JOUR

T1 - Nucleophilic addition to N-alkoxyamides

AU - Satou, Takaaki

AU - Chida, Noritaka

PY - 2014/5/28

Y1 - 2014/5/28

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84899074644&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899074644&partnerID=8YFLogxK

U2 - 10.1039/c4ob00389f

DO - 10.1039/c4ob00389f

M3 - Article

VL - 12

SP - 3147

EP - 3150

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 20

ER -