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Stereoselective Synthesis of Tropanes via a Retro-6 p Electrocyclic Ring-Opening / Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles. Stereoselektive Synthese von Tropanen über eine 6π-elektrocyclische Ringöffnung/ Huisgen-[3+2]-Cycloadditionskaskade von monocyclopropanierten Heterocyclen

URN to cite this document:
urn:nbn:de:bvb:355-epub-445791
DOI to cite this document:
10.5283/epub.44579
Sonnleitner, Carina M. ; Park, Saerom ; Eckl, Robert ; Ertl, Thomas ; Reiser, Oliver
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Date of publication of this fulltext: 25 Jan 2021 08:02


Abstract

The synthesis of tropanes via a microwave-assisted, stereoselective 6 pi-electrocyclic ring-opening/ Huisgen [3+2]-cycloaddition cascade of cyclopropanated pyrrole and furan derivatives with electron-deficient dipolarophiles is demonstrated. Starting from furans or pyrroles, 8-aza- and 8-oxabicyclo[3.2.1]octanes are accessible in two steps in dia- and enantioselective pure form, being versatile ...

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