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
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) un...
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Published in | Synthesis (Stuttgart) Vol. 51; no. 22; pp. 4296 - 4310 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
01.11.2019
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Subjects | |
Online Access | Get more information |
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Summary: | 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. |
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ISSN: | 0039-7881 1437-210X |
DOI: | 10.1055/s-0039-1690619 |