H. Malinakova, Sandeep N. Raikar, Lucas F. McCormick
Jul 23, 2014
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Journal
Tetrahedron Letters
Abstract
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.