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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Published inAngewandte Chemie (International ed.) Vol. 49; no. 36; pp. 6369 - 6372
Main Authors Shirokane, Kenji, Kurosaki, Yusuke, Sato, Takaaki, Chida, Noritaka
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 23.08.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
allylation
amides
Amides - chemistry
Amines - chemistry
Chemistry
Chemistry, Multidisciplinary
cyanation
Cyclization
Imines - chemistry
macrocycles
Macrocyclic Compounds - chemistry
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
amides
ASYMMETRIC-SYNTHESIS
STEREOSELECTIVE CYCLIZATION
IMINIUM ION
cyclization
INTRAMOLECULAR REACTIONS
cyanation
GENERAL-SYNTHESIS
macrocycles
ALPHA-ACETOXY ETHERS
MONOSILYL ACETALS
VERSATILE CONVERSION
DIBALH REDUCTION
AMIDE BOND FORMATION
allylation
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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.
Bibliography:http://dx.doi.org/10.1002/anie.201001127
istex:715D6CF127FED6A8B705C05898DFDA68B126B70A
ark:/67375/WNG-V8KWSZ1S-8
ArticleID:ANIE201001127
This research was supported by a Grant-in-Aid for Young Scientists (B) from MEXT (21750049) and the Otsuka Pharmaceutical Co. Award in Synthetic Organic Chemistry (Japan).
MEXT - No. 21750049
This research was supported by a Grant‐in‐Aid for Young Scientists (B) from MEXT (21750049) and the Otsuka Pharmaceutical Co. Award in Synthetic Organic Chemistry (Japan).
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001127