Modular strategy for the synthesis of functionalized aryl-fused azabicyclo[2.2.2]octanes via radical-mediated cascade cyclization |
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| Authors: | Helena C. Malinakova Sandeep N. Raikar Lucas F. McCormick |
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| Affiliation: | Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, United States; Center of Excellence in Chemical Methodologies and Library Development, The University of Kansas, 2034 Becker Drive, Lawrence, KS, 66047, United States |
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| Abstract: | A two-step synthesis of rare 2-azabicyclo[2.2.2]octanes is described. N-propargyl amides obtained via Cu(I)-catalyzed three-component coupling, underwent radical-mediated cascade cyclization to afford 5,6-aryl-fused 2-azabicyclo[2.2.2]octanes with arylidene functionality on the two-carbon bridge in 43–62% yields. Phenylidene and 1-naphtylidene derivatives were obtained exclusively as Z diastereomers, whereas electron rich groups in the arylidene substituent afforded product mixtures favoring the Z diastereomer by 2.3:1 M ratio. |
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| Keywords: | Azabicyclo[2.2.2]octanes Radical cyclization Three-component coupling, N-heterocycles |
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