A new supported reagent for the parallel synthesis of primary and secondary O-alkyl hydroxylamines through a base-catalyzed Mitsunobu reaction

LT Maillard, M Benohoud, P Durand…

Index: Maillard, Ludovic T.; Benohoud, Meryem; Durand, Philippe; Badet, Bernard Journal of Organic Chemistry, 2005 , vol. 70, # 16 p. 6303 - 6312

Full Text: HTML

Citation Number: 20

Abstract

The growing field of applications of O-alkyl hydroxylamines in medicinal chemistry and chemical biology has motivated the search for a parallel synthesis. A solid-phase approach based on the alkylation by alcohols of a new supported N-hydroxyphthalimide reagent using a Mitsunobu reaction followed by methylaminolysis has been optimized. This study points out the importance of the linker and a specific base effect for the Mitsunobu reaction. A ...