Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions

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...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2010-08, Vol.49 (36), p.6369-6372
Main Authors: Shirokane, Kenji, Kurosaki, Yusuke, Sato, Takaaki, Chida, Noritaka
Format: Article
Language:English
Subjects:
allylation
amides
Amides - chemistry
Amines - chemistry
cyanation
Cyclization
Imines - chemistry
macrocycles
Macrocyclic Compounds - chemistry
Organometallic Compounds - chemistry
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001127