Chemoselective Amide Formation Using O-(4-Nitrophenyl) hydroxylamines and Pyruvic Acid Derivatives

S Kumar, R Sharma, M Garcia, J Kamel…

Index: Kumar, Sonali; Sharma, Rashi; Garcia, Megan; Kamel, Joseph; McCarthy, Caroline; Muth, Aaron; Phanstiel, Otto Journal of Organic Chemistry, 2012 , vol. 77, # 23 p. 10835 - 10845

Full Text: HTML

Citation Number: 8

Abstract

A series of O-(4-nitrophenyl) hydroxylamines were synthesized from their respective oximes using a pulsed addition of excess NaBH3CN at pH 3 in 65–75% yield. Steric hindrance near the oxime functional group played a key role in both the ease by which the oxime could be reduced and the subsequent reactivity of the respective hydroxylamine. Reaction of the respective hydroxylamines with pyruvic acid derivatives generated the desired amides in ...