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Copper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes. | LitMetric

AI Article Synopsis

  • The text discusses a copper catalyst that facilitates the addition of phosphines to cyclopropenes at room temperature, resulting in high yields and selectivity.
  • It highlights the ability to create various cyclopropylphosphines with different properties and demonstrates the enrichment of phosphorus stereocenters using a method called Dynamic Kinetic Asymmetric Transformation (DyKAT).
  • Additionally, it details the mechanistic insights from experimental and theoretical studies, indicating that the rate-determining step involves the insertion of a copper-phosphido complex into a carbon-carbon double bond, followed by a specific protodemetalation process.

Article Abstract

We describe a copper catalyst that promotes the addition of phosphines to cyclopropenes at ambient temperature. A range of cyclopropylphosphines bearing different steric and electronic properties can now be accessed in high yields and enantioselectivities. Enrichment of phosphorus stereocenters is also demonstrated via a Dynamic Kinetic Asymmetric Transformation (DyKAT) process. A combined experimental and theoretical mechanistic study supports an elementary step featuring insertion of a Cu -phosphido into a carbon-carbon double bond. Density functional theory calculations reveal migratory insertion as the rate- and stereo-determining step, followed by a syn-protodemetalation.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11365472PMC
http://dx.doi.org/10.1002/anie.202306511DOI Listing

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