A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions

Kenji Shirokane; Kurosaki Yusuke; Takaaki Sato; Noritaka Chida

doi:10.1002/anie.201001127

A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions

Kenji Shirokane, Kurosaki Yusuke, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

105 Citations (Scopus)

Abstract

Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.

Original language	English
Pages (from-to)	6369-6372
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	36
DOIs	https://doi.org/10.1002/anie.201001127
Publication status	Published - 2010 Aug 23

Keywords

Allylation
Amides
Cyanation
Cyclization
Macrocycles

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201001127

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abstract = "Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.",

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AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2010/8/23

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N2 - Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.

AB - Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.

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KW - Amides

KW - Cyanation

KW - Cyclization

KW - Macrocycles

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A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions

Abstract

Keywords

ASJC Scopus subject areas

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