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- W2123249178 abstract "The Pd/phosphine-catalyzed reaction of 1 with aryl bromides leads to the selective synthesis of either 6-aryl octahydrocyclopenta[b]pyrroles (3), the corresponding 5-aryl isomers 5, diarylamine 2, or hexahydrocyclopenta[b]pyrrole 4 depending on the structure of the phosphine ligand. These transformations are effective with a variety of different aryl bromides and provide 3−5 with excellent levels of diastereoselectivity (dr ≥ 20:1). The changes in product distribution are believed to derive from the influence of Pd-catalyst structure on the relative rates of reductive elimination, β-hydride elimination, alkene insertion, and alkene displacement processes in a mechanistically complex reaction. The effect of phosphine ligand structure on product distribution is described in detail, along with analysis of a proposed mechanism for these transformations." @default.
- W2123249178 created "2016-06-24" @default.
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- W2123249178 date "2005-05-27" @default.
- W2123249178 modified "2023-10-16" @default.
- W2123249178 title "Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[<i>b</i>]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction" @default.
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- W2123249178 doi "https://doi.org/10.1021/ja0430346" @default.
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