Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2005(3): 0357-0357
DOI: 10.1055/s-2005-921613
DOI: 10.1055/s-2005-921613
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
A New Supported Reagent for the Parallel Synthesis of O-Alkyl Hydroxylamines
L. T. Maillard, M. Benohoud, P. Durand*, B. Badet
Institut de Chimie des Substances Naturelles, Gif-Sur-Yvette, France
Further Information
Publication History
Publication Date:
22 November 2005 (online)
Significance
A new Merrifield resin-supported N-hydroxyphthalimide reagent was developed for the parallel synthesis of O-alkyl hydroxylamines. The triazole-linked N-hydroxyphthalimide resin 1 was identified to be most effective when imidazole-mediated Mitsunobu conditions (5 equiv of ROH/PPh3/DIAD/imidazole) were employed. The subsequent methylaminolysis of the resulting alkoxyphthalimide 2 gave O-alkyl hydroxylamines in moderate to high yields (up to 100%) with high purities (up to >99%). Parallel synthesis of 40 types of O-alkyl hydroxylamines was demonstrated.