Beilstein J. Org. Chem.2009,5, No. 69, doi:10.3762/bjoc.5.69
place to afford cis-2,4-diaryl-substituted pyrrolidines 35–37.
Keywords: cyclic sulfonamides; diastereoselective alkene functionalisation; doublereduction; Pd-mediated cross coupling; Introduction
Substituted pyrrolidine ring systems represent a common structural motif in a range of biologically
active compounds, including pharmaceutical agents and natural products. In relation to these general targets, we have recently developed a method that enables the construction of aryl-substituted pyrrolidines, featuring the doublereduction of cyclic aromatic sulfonamides [1][2][3][4]. As illustrated in
structure was implicated in the lack of epoxide reactivity, doublereduction of 7a was then considered. It was hoped that following N–S bond cleavage, the now electron rich amino species would form an imine 9 that would then undergo further reduction to afford 11. However, in the event the only isolable
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Graphical Abstract
Scheme 1:
The diastereoselective intramolecular Heck-hydrogenation and double reduction sequence as a means o...