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• W2149352105 abstract "[136779-28-7] C22H36P2 (MW 362.47)InChI = 1S/C22H36P2/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4/h9-12,17-20H,5-8,13-16H2,1-4H3/t17-,18-,19-,20-/m0/s1InChIKey = GVVCHDNSTMEUCS-MUGJNUQGSA-N(ligand for asymmetric catalysis; rhodium(I) complexes are efficient catalysts in highly enantioselective hydrogenation of various unsaturated substrates [enol acylates,1, 2 (N-acylamino)acrylates,1, 3, 4 and N-acylhydrazones5])Alternate Name: (S,S)-ethyl-DuPHOSPhysical Data: bp 138–145 °C/0.04 mmHg; [α]D +265 (c 1, hexane).Solubility: soluble in most organic solvents.Form Supplied in: colorless oil; commercially available.Analysis of Reagent Purity: optical rotation; NMR spectroscopy.Preparative Methods: the preparation of (S,S)-ethyl-DuPHOS is based on (3R,6R)-octane-3,6-diol as an enantiomerically pure starting compound.1, 3 The latter is synthesized by a three-step procedure6, 7 starting from methyl 3-oxopentanoate, which is transformed to methyl (R)-3-hydroxypentanoate (99% ee) by enantioselective hydrogenation with a Ru-(R)-BINAP catalyst,8 followed by hydrolysis to the hydroxy acid. The subsequent electrochemical Kolbe coupling reaction leads to (3R,6R)-octane-3,6-diol in a protocol that can be scaled up to multigram quantities (eq 1).3, 6(1)The chiral octanediol in turn is converted into the corresponding cyclic sulfate by reaction with thionyl chloride and subsequent oxidation with sodium periodate and a catalytic amount of ruthenium(III) chloride (0.1 mol%) (eq 2).3 In the final step, 1,2-diphosphinobenzene9 is lithiated by treatment with n-butyllithium (n-BuLi; 2 equiv, 1.6 mol% in hexane) followed by the addition of the (3R,6R)-octane-3,6-diol cyclic sulfate (2 equiv) and a further addition of 2.2 equiv of n-BuLi. (S,S)-Ethyl-DuPHOS is obtained in a yield of over 70% [78% yield was described for the (R,R)-enantiomer by an analogous method3].1 In addition to (S,S)-ethyl-DuPHOS, a variety of related bisphospholanes either linked by an ethylene bridge, or bearing other 2,5-alkyl substituents, or with opposite configuration have been prepared by this methodology.1, 3(2)Handling, Storage, and Precautions: the reagent is sensitive to air and should be handled and stored under argon or nitrogen." @default.
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• W2149352105 date "2002-04-15" @default.
• W2149352105 modified "2023-09-24" @default.
• W2149352105 title "(S,S)-1,2-Bis(2,5-diethylphospholano)benzene" @default.
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• W2149352105 doi "https://doi.org/10.1002/047084289x.rn00004" @default.
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