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Title
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Expedient synthesis of bridged bicyclic nitrogen scaffolds via orthogonal tandem catalysis
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Author
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Abstract
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| Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed g-C(sp(3))-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed g-C(sp(3))-H olefination is achieved. |
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Language
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English
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Source (journal)
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Angewandte Chemie: international edition in English. - Weinheim
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Publication
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Weinheim
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Wiley-v c h verlag gmbh
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2021
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ISSN
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1433-7851
0570-0833
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DOI
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10.1002/ANIE.202106716
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Volume/pages
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60
:40
(2021)
, p. 21988-21996
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ISI
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000683678800001
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Pubmed ID
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34143924
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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