Resolved P-Metalated Nucleoside Phosphoramidites

Miller, Erica J.; Garcia, Kevin J.; Holahan, Erin C.; Ciccarelli, Rosa M.; Bergin, Rachel; Casino, Stephanie L.; Bogaczyk, Tyler L.; Krout, Michael R.; Findeis, Peter M.; Stockland, Robert A.

doi:10.1021/ic5024357

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Stereospecific Protodeauration/Transmetalation Generating Configurationally Stable P‐Metalated Nucleoside Derivatives

et al. 2018

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Highly efficient transmetalation between gold phosphites and iodopalladium species is presented. In addition to successful transfer of cyclic and acyclic phosphites, studies involving P‐chiral substrates revealed that an initial protodeauration as well as the target transmetalation were both stereospecific, and that the overall process occurred with retention of configuration at phosphorus. Building on the mechanistic work, a catalytic approach to the synthesis of chiral P‐arylated nucleoside derivatives was developed. This chemistry has the potential to be easily adapted for the preparation of a diverse group of P‐chiral species.

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