1997
DOI: 10.1021/ic961280f
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Oxidation of Thioether Ligands in Pseudotetrahedral Cyclopentadienylruthenium Complexes:  Toward a New Stereoselective Synthesis of Chiral Sulfoxides1

Abstract: Ionic ruthenium thioether complexes [Cp(LL')Ru(SRR')]PF(6) (LL' = Ph(2)PCH(2)PPh(2) (1), Ph(2)PC(2)H(4)PPh(2) (2), (Ph(3)P, CO) (3), Me(2)PC(2)H(4)PPh(2) (4), (S,S)-Ph(2)PCHMeCHMePPh(2) (5), SRR' = MeSPh (a), MeS-i-Pr (b), MeSBz (c), i-PrSBz (d), EtSBz (e), MeSCy (f), SC(4)H(8) (g)) were synthesized from the corresponding chloro complexes [Cp(LL')RuCl] and thioethers. 5a crystallized in the orthorhombic system, space group P2(1)2(1)2(1) (No. 19), with a = 11.269(3) Å, b = 15.104(2) Å, c = 23.177(4) Å, and Z = … Show more

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Cited by 46 publications
(18 citation statements)
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“…Recently, the asymmetric oxidation of thioethers to sulfoxides by a metal catalysis strategy has attracted great attention. [6,7] A new approach for the synthesis of chelate sulfoxide compounds with ee values of up to 98.9 % by means of oxidation of a coordinated thioether to a sulfoxide in situ in a chiral-at-metal asymmetric environment, followed by release of the oxidized ligand, has been developed by our group. [8] In these processes, the absolute configuration at the metal center is each case completely retained during the formation of the thioether complex, the oxidation in situ to generate the sulfoxide complex, and the release of the sulfoxide ligand.…”
Section: Introductionmentioning
confidence: 99%
“…Recently, the asymmetric oxidation of thioethers to sulfoxides by a metal catalysis strategy has attracted great attention. [6,7] A new approach for the synthesis of chelate sulfoxide compounds with ee values of up to 98.9 % by means of oxidation of a coordinated thioether to a sulfoxide in situ in a chiral-at-metal asymmetric environment, followed by release of the oxidized ligand, has been developed by our group. [8] In these processes, the absolute configuration at the metal center is each case completely retained during the formation of the thioether complex, the oxidation in situ to generate the sulfoxide complex, and the release of the sulfoxide ligand.…”
Section: Introductionmentioning
confidence: 99%
“…A similar opening of the thiolactolate could be achieved with various Lewis acids. Thus, Within a few days complete conversion into the free monothioacetal 7a and the known iodo complex 8 [12] took when LiBF 4 was added to a solution of 5b in acetone and the solvent removed under reduced pressure, a color change place. Chromatographic separation yielded 7a as an impure yellow oil, which was identified spectroscopically.…”
Section: Resultsmentioning
confidence: 99%
“…In this context it should be mentioned that the cleavage of thioether ligands from halfsandwich ruthenium complexes can be achieved under mild conditions. [52][53][54] …”
Section: Discussionmentioning
confidence: 99%