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- W2105737689 abstract "[528854-26-4] C52H48P2 (MW 734.89)InChI = 1S/C52H48P2/c1-51(2,3)53-31-37-25-23-33-15-7-11-19-39(33)45(37)47-41-21-13-9-17-35(41)27-29-43(47)49(53)50-44-30-28-36-18-10-14-22-42(36)48(44)46-38(32-54(50)52(4,5)6)26-24-34-16-8-12-20-40(34)46/h7-30,49-50H,31-32H2,1-6H3/t49-,50-,53?,54?/m1/s1InChIKey = YXMFQIWDFKIXGQ-JBOWJRQASA-N(optically active reagent used as a ligand for asymmetric catalysis; the rhodium(I) complexes are highly enantioselective catalysts in homogeneous asymmetric hydrogenation reactions)Alternate Name: (S)-Binapine.Physical Data: mp 375–379 °C.Solubility: soluble in THF, CH2Cl2, and other common organic solvents.Analysis of Reagent Purity: optical rotation; NMR spectroscopy.Form Supplied in: colorless crystals, Sigma–Aldrich.Preparative Method: the Binapine ligands are readily synthesized from (S)-2,2′-dimethylbinaphthyl (eq 1).1 Double metalation of enantiomerically pure (S)-2,2′-dimethylbinaphthyl with n-BuLi/TMEDA followed by reaction with t-BuPCl2 and sulfur yielded the binaphthophosphepine sulfide in 61% yield. Deprotonation of sulfide with t-BuLi/TMEDA followed by coupling mediated by CuCl2 provided disulfide as a single isomer in 25% yield, which was desulfurized with hexachlorodisilane to afford (S)-Binapine in 90% yield. (1)Purification: passing through a short silica gel plug under N2 afforded the pure compound.Handling, Storage, and Precautions: although exposure of the ligand to air for several days did not yield any detectable oxidation product,1 the reagent is still considered air sensitive and should be handled and stored under an inert atmosphere. Toxicity data are not available." @default.
- W2105737689 created "2016-06-24" @default.
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- W2105737689 date "2011-09-15" @default.
- W2105737689 modified "2023-09-24" @default.
- W2105737689 title "(3R,3′R,4S,4′S,11bS,11′bS)-4,4′-Bis(1,1-dimethylethyl)-4,4′,5,5′-tetrahydro-3,3′-bi-3H-dinaphtho[2,1-c:1′,2′-e]phosphepin" @default.
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- W2105737689 doi "https://doi.org/10.1002/047084289x.rn01362" @default.
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