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A Direct Entry to Substituted N ‐Methoxyamines from N ‐Methoxyamides via N ‐Oxyiminium Ions
Author(s) -
Shirokane Kenji,
Kurosaki Yusuke,
Sato Takaaki,
Chida Noritaka
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201001127
Subject(s) - ion , chemistry , organic chemistry
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.