Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides

Xiaobing Chen, Damián Padin Santos*, Lotte Stindt, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)
236 Downloads (Pure)

Abstract

P-stereogenic compounds are widely used as ligands in asymmetric catalysis and are present in a myriad of bioactive compounds and pharmaceuticals. Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral-at-P alkenylphosphonamidates through a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo- and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P-stereogenic compounds.

Original languageEnglish
Article numbere202307450
Number of pages8
JournalAngewandte Chemie (International ed. in English)
Volume62
Issue number33
Early online date6-Jul-2023
DOIs
Publication statusPublished - 14-Aug-2023

Keywords

  • Asymmetric Synthesis
  • Chiral Auxiliaries
  • Cross-Coupling
  • Nickel
  • Phosphorus

Cite this