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Rudy, Heinrich-Karl A.; Wanner, Klaus T. (2019): Accessing Tricyclic Imines Comprising a 2-Azabicyclo[2.2.2]octane Scaffold by Intramolecular Hetero-Diels-Alder Reaction of 4-Alkenyl-Substituted N-Silyl-1,4-dihydropyridines. In: Synthesis-Stuttgart, Vol. 51, No. 22: pp. 4296-4310
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Abstract

Tricyclic imines inheriting a 2-azabicyclo[2.2.2]octane (isoquinuclidine) scaffold were provided with high regioselectivity in moderate to very good yields by a smooth, broadly applicable intramolecular hetero-Diels-Alder reaction of various 4-omega-alkenyl-substituted 1,4-dihydropyridines (DHPs) under trifluoroacetic acid catalysis. The required- 4,4-disubstituted 1,4-DHPs were obtained by introduction of omega-alkenyl moieties of varying chain length via diorganomagnesium reagents into the 4-position of diversely 4-substituted pyridines after prior N-activation with triisopropylsilyltriflate.