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).
A Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions†
Article first published online: 29 JUL 2010
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 49, Issue 36, pages 6369–6372, August 23, 2010
How to Cite
Shirokane, K., Kurosaki, Y., Sato, T. and Chida, N. (2010), A Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions. Angew. Chem. Int. Ed., 49: 6369–6372. doi: 10.1002/anie.201001127
- Issue published online: 19 AUG 2010
- Article first published online: 29 JUL 2010
- Manuscript Revised: 9 JUN 2010
- Manuscript Received: 24 FEB 2010
- MEXT. Grant Number: 21750049
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.