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Diversity in Gold-Catalyzed Formal Cycloadditions of Ynamides with Azidoalkenes or 2H-Azirines: [3+2] versus [4+3]
Samir Kundlik Pawar1, Rajkumar Lalji Sahani1, Rai-Shung Liu2
1Department of Chemistry, National Tsing-Hua University, Hsinchu 30013 (Taiwan).
Abstract:
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 Cβ -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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