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J Org Chem. 2002 Aug 23;67(17):6236-9.

Comparison of electrophilic amination reagents for N-amination of 2-oxazolidinones and application to synthesis of chiral hydrazones.

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  • 1Department of Chemistry, Cook Physical Science Building, University of Vermont, Burlington, Vermont 05405, USA.


Comparison of several hydroxylamine-based electrophilic ammonia equivalents in the N-amination of 2-oxazolidinones revealed that O-(p-nitrobenzoyl)hydroxylamine (NbzONH(2)) and sodium hydride in dioxane is a superior reagent combination for this purpose. Practical preparations of a variety of chiral N-acylhydrazones by this method gave yields ranging from 45 to 95%. Methods for exchange or removal of the aldehyde component have been developed, making this a general route to chiral N-acylhydrazones of interest for asymmetric synthesis applications.

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