Synthesis and Cycloaddition Reactions of 2,3,4,5-Tetrahydropyrazine 1-Oxide

The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 37; pp. 7229 - 7236
Main Authors Wazeer, Mohammed I.M, Perzanowski, Herman P, Qureshi, Sajid I, Al-Murad, Mohammad B, Asrof Ali, Sk
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.09.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
cycloadditions
nitrones
Physical Sciences
regiochemistry
Science & Technology
stereochemistry
stereochemistry
regiochemistry
cycloadditions
nitrones
NITRONE
CONFORMATIONAL-ANALYSIS
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Summary:The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00574-3