Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 30, Pages 10843-10850Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500694
Keywords
cycloaddition; gold; homogeneous catalysis; reaction mechanisms; structure elucidation
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Funding
- National Science Council, Taiwan
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Gold-catalyzed cycloadditions of ynamides with azidoalkenes or 2H-azirines give [3+2] or [4+3] formal cycloadducts of three classes. Cycloadditions of ynamides with 2H-azirine species afford pyrrole products with two regioselectivities when the C-substituted 2H-azirine is replaced from an alkyl (or hydrogen) with an ester group. For ynamides substituted with an electron-rich phenyl group, their reactions with azidoalkenes proceed through novel [4+3] cycloadditions to deliver 1H-benzo[d]azepine products instead.
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