4.7 Article

One-ligand Catalytic Asymmetric Deprotonation of a Phosphine Borane: Synthesis of P-Stereogenic Bisphosphine Ligands

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 11, Pages 4794-4799

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo200708e

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Funding

  1. EPSRC
  2. F. Hoffmann-La Roche Ltd
  3. EU

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A new protocol for the catalytic asymmetric deprotonation of a phosphine borane using s-BuLi and sub-stoichiometric quantities of chiral diamines is reported. The method involves three sequential additions of s-BuLi, and use of (-)-sparteine or the (+)-sparteine surrogate facilitates access to P-stereogenic phosphines with opposite configuration. The method is exemplified by the catalytic asymmetric synthesis of each enantiomer of precursors to QuinoxP*, trichickenfootphos, and Mini-PHOS.

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