4.8 Article

Ru(II) Complexes of N-Alkylated TsDPEN Ligands in Asymmetric Transfer Hydrogenation of Ketones and Imines

Journal

ORGANIC LETTERS
Volume 11, Issue 4, Pages 847-850

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol802801p

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Funding

  1. EPSRC [EP/F019424/1]
  2. EPSRC National Mass Spectroscopic service (Swansea)
  3. Advantage West Midlands (AWM)
  4. European Regional Development Fund (ERDF)
  5. EPSRC [EP/F019424/1] Funding Source: UKRI
  6. Engineering and Physical Sciences Research Council [EP/F019424/1] Funding Source: researchfish

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N-Alkylated TsDPEN derivatives bearing a small alkyl group act as highly efficient ligands in Ru(II) complexes for the asymmetric transfer hydrogenation of imines and ketones. A larger alkyl group serves to significantly reduce the activity of the catalyst; however, high enantiomeric excesses are still obtained. An X-ray crystal structure of the N-benzyl derivative reveals a conformation that permits hydrogen transfer through a six-membered transition state. A transition state structure for the imine reduction process is proposed.

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