A Novel, General Method for the Synthesis of Nitrile Oxides: Dehydration of O-Silylated Hydroxamic Acids
- 1 February 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (4) , 539-541
- https://doi.org/10.1021/ol991396q
Abstract
[reaction: see text] O-Silylated hydroxamic acids serve as stable, readily accessible, crystalline precursors to nitrile oxides when treated with trifluoromethanesulfonic anhydride and triethylamine. Under these mild conditions in the presence of olefins O-silylated hydroxamic acids afford isoxazoline cycloadducts. This procedure represents a novel, general method for the one-step generation of nitrile oxides, which complements existing protocols.Keywords
This publication has 17 references indexed in Scilit:
- Enantioselective Synthesis of ent-Stellettamide A via a Novel Dipolar Cycloaddition Reaction of (Trimethylsilyl)diazomethaneThe Journal of Organic Chemistry, 1997
- Asymmetric Dipolar Cycloadditions of Me3SiCHN2. Synthesis of a Novel Class of Amino Acids: AzaprolinesJournal of the American Chemical Society, 1997
- Synthesis of Amphotericin B. A Convergent Strategy to the Polyol Segment of the Heptaene Macrolide AntibioticsThe Journal of Organic Chemistry, 1996
- The vinylogous anomeric effect in 3-alkyl-2-chlorocyclohexanone oximes and oxime ethersJournal of the American Chemical Society, 1990
- Reinvestigation of the Base-Induced Ring Closure of Methylsulfonium Salts of N-Trityl-(S)-methioninehydroxamide and Derivatives.Acta Chemica Scandinavica, 1990
- Synthesis and characterization of mixed anhydrides of O-benzylbenzohydroximic acidCollection of Czechoslovak Chemical Communications, 1989
- Oxidative fragmentation of .beta.-stannyl oximes: stereospecific formation of unsaturated nitrile oxidesJournal of the American Chemical Society, 1985
- O-Trimethylsilyl hydroxamoyl chlorides as nitrile oxide precursorsThe Journal of Organic Chemistry, 1983
- The Reactions of Primary Nitroparaffins with Isocyanates1Journal of the American Chemical Society, 1960
- Ueber BenzhydroximsäurechloridEuropean Journal of Inorganic Chemistry, 1894