Lewis acid catalyzed three-component hetero-Diels-Alder (Povarov) reaction of N-arylimines with strained norbornene-derived dienophiles

Authors :: Smith, Chris D.
Gavrilyuk, Julia I.
Lough, Alan J.
Batey, Robert A.
Source :: Journal of Organic Chemistry. Feb 5, 2010, Vol. 75 Issue 3, 702-715
Publication Year :: 2010
Abstract: The introduction of ring strain in the dienophile, as with moderately strained bicycle[2.2.1]heptenes (norbornene), has enabled three-component Povarov reaction with in situ formed N-arylimines under Lewis acid catalyzed conditions (B[F.sub.3].O[Et.sub.2]). The preference for the formation of exo-exo diastereomic adducts is seen in most cases, but the formation of exo-endo adducts is observed for reactions of ortho- or meta-substituted anilines.

Subjects :: Aromatic amines -- Chemical properties
Aromatic amines -- Structure
Aniline -- Chemical properties
Aniline -- Structure
Aldehydes -- Chemical properties
Aldehydes -- Structure
Hydroquinone -- Chemical properties
Hydroquinone -- Structure
Diels-Alder reaction -- Usage
Biological sciences
Chemistry

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