142941-79-5Relevant academic research and scientific papers
BROMONITRILE OXIDE CYCLOADDITIONS IN WATER
Rohloff, John C.,Robinson, James III,Gardner, John O.
, p. 3113 - 3116 (2007/10/02)
Bromonitrile oxide can be generated homogeneously in water at acidic pH, allowing efficient cycloaddition with water soluble olefins and acetylenes.Allylammonium salts react with high regioselectivity and without the need for N-group protection. Keyword: Acivicin; transglutaminase; cysteine; 4,5-dihydroisoxazole; dibromonoformaldoxime.
NITRILE OXIDES IN MEDICINAL CHEMISTRY-- 2. SYNTHESIS OF THE TWO ENANTIOMERS OF DIHYDROMUSCIMOL
Amici, Marco De,Micheli, Carlo De,Misani, Valeria
, p. 1975 - 1986 (2007/10/02)
The cycloaddition of bromonitrile oxide to monosubstituted olefins has a high regioselectivity yielding 3-bomo-5-substituted isoxazolines contaminated by minor amounts (4-9percent) of the 4-substituted isomer.The adducts of bromonitrile oxide to allyl alcohol and N-protected allylamine were employed as key intermediates in the preparation of racemic dihydromuscimol (DHM).The synthesis of (R)-(-)- and (S)-(+)-DHM was accomplished by using the two diastereomers obtained by the cycloaddition of bromonitrile oxide to (S)-(+)-isopropylidene-3-buten-1,2-diol.The enantiomeric excess of R)-(-)- and (S)-(+)-DHM, determined by capillary GLC on the appropriate precursors, were 98.8 and >99.0 percent.A spectroscopic survey of the tautomerism of 3-hydroxyisoxazolines indicates the predominant or exclusive occurence of the NH form.
