Four-component Pd-catalysed cascade/ring closing metathesis. Synthesis of heterocyclic enones |
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| Authors: | Ronald Grigg William Martin Visuvanathar Sridharan |
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| Institution: | a Molecular innovation, Diversity and Automated Synthesis (MIDAS) Centre, School of Chemistry, Leeds University, Leeds LS2 9JT, UK
b Process Research and Development, GlaxoSmithKline, Gunnels Wood Road, Stevenage SG1 2NY, UK |
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| Abstract: | A palladium-catalysed four-component process is described involving carbon monoxide, allene and aryl/heteroaryl iodides generating (π-allyl) palladium species, which are intercepted by alkene tethered nitrogen nucleophiles to afford 1,6- and 1,7-dienones. Subsequent ring closing metathesis affords five- and six-membered N-heterocyclic enones. The N-heterocyclic enones are active dipolarophiles in 1,3-dipolar cycloaddition reactions as exemplified by azomethine ylide and nitrone cycloadditions. |
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| Keywords: | Ring closing metathesis Catalytic cascades Heterocyclic enones 1 3-Dipolar cycloadditions |
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