| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - A Molybdenum-Catalyzed Oxidative System Forming Oxazines(Hetero-Diels−Alder Adducts) from Primary Aromatic Amines,Hydrogen Peroxide, and Conjugated Dienes
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - The development of a new molybdenum-catalyzed procedurefor the formation of oxazineshetero-Diels−Alder adductsfrom primary aromatic amines, hydrogen peroxide,and conjugated dienesis presented. The method is based on a molybdenum−peroxocomplex, which in the presence ofhydrogen peroxide as the terminal oxidant selectively catalyzes theoxidation of primary aromaticamines to the corresponding dienophilic nitroso compounds. Themolybdenum−peroxo catalyst isunder the present reaction conditions not reactive toward conjugateddienes and substituentsattached to the aromatic nuclei of the primary aromatic amines.Several oxazines are synthezisedfollowing this new procedure using primary aromatic amines havingeither electron-withdrawingor electron-donating substituents and 1,3-cyclohexadiene as thestandard diene. The scope of thenew procedure is also demonstrated by the preparation of severaloxazines using different alkyl-and phenyl-substituted conjugated dienes and 4-chloroaniline asprecursor for the dienophile.Moderate diastereomeric excesses are found when the reaction iscarried out with 1-(2-aminophenyl)ethanol and 1,3-cyclohexadiene or (E)-1-phenyl-1,3-butadiene.The stereochemical and electronicfactors governing the reaction course are brieflydiscussed.
|
| article type
| |
| is part of this journal
| |
