Enantioselective syntheses of sulfoxides in octahedral ruthenium(II) complexes via a chiral-at-metal strategy

Inorganic Chemistry
Zheng-Zheng LiBao-Hui Ye

Abstract

The preparation of chiral 2-(alkylsulfinyl)phenol compounds by enantioselective coordination-oxidation of the thioether ruthenium complexes with a chiral-at-metal strategy has been developed. The enantiomerically pure sulfoxide complexes Δ-[Ru(bpy)2{(R)-LO-R}](PF6) (bpy is 2,2'-bipyridine, HLO-R is 2-(alkylsulfinyl)phenol, R = Me (Δ-1a), Et (Δ-2a), iPr (Δ-3a), Bn (Δ-4a), and Nap (Δ-5a)) and Λ-[Ru(bpy)2{(S)-LO-R}](PF6) (R = Me (Λ-1a), Et (Λ-2a), iPr (Λ-3a), Bn (Λ-4a), and Nap (Λ-5a)) have been synthesized by the reaction of Δ-[Ru(bpy)2(py)2](2+) or Λ-[Ru(bpy)2(py)2](2+) with the prochiral thioether ligands 2-(alkylthio)phenol (HL-R), followed by enantioselective oxidation with m-CPBA as oxidant. The X-ray crystallography was used to verify the stereochemistry of ruthenium complexes and sulfur atoms. The configurations of the ruthenium complexes are stable during the coordination and oxidation reactions. Moreover, the chiral sulfoxide ligands are enantioselectively generated by controlling of the configuration of ruthenium centers in the course of oxidation reaction. That is, the Λ configuration at the ruthenium center generates the S sulfoxide ligand; on the contrary, the Δ configuration of the ruthenium complex originates the R...Continue Reading

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Citations

Mar 16, 2017·Journal of the American Chemical Society·Yu ZhengEric Meggers
Mar 22, 2016·Organic & Biomolecular Chemistry·Yani TangSimon Duttwyler
Aug 8, 2017·Chemistry, an Asian Journal·Lilu Zhang, Eric Meggers
Sep 22, 2019·Chemistry : a European Journal·Philipp S SteinlandtEric Meggers
Apr 30, 2020·Chemical Reviews·Elżbieta Wojaczyńska, Jacek Wojaczyński
Dec 15, 2018·Inorganic Chemistry·Li-Ping LiBao-Hui Ye
Jan 6, 2021·Journal of the American Chemical Society·Sebastian B VittardiJeffrey J Rack
Dec 12, 2018·Journal of the American Chemical Society·Lucien N LameijerSylvestre Bonnet

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