Journal article
Comparison of electrophilic amination reagents for N-amination of 2-oxazolidinones and application to synthesis of chiral hydrazones
Journal of organic chemistry, Vol.67(17), pp.6236-6239
08/23/2002
DOI: 10.1021/jo0259663
PMID: 12182669
Abstract
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.
Details
- Title: Subtitle
- Comparison of electrophilic amination reagents for N-amination of 2-oxazolidinones and application to synthesis of chiral hydrazones
- Creators
- Yuehai Shen - Department of Chemistry, Cook Physical Science Building, University of Vermont, Burlington, Vermont 05405, USAGregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.67(17), pp.6236-6239
- DOI
- 10.1021/jo0259663
- PMID
- 12182669
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Grant note
- P41RR00954 / NCRR NIH HHS
- Language
- English
- Date published
- 08/23/2002
- Academic Unit
- Chemistry
- Record Identifier
- 9983985955802771
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