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- W4234729795 abstract "[184034-09-1] C25H14Cl2O5 (MW 465.28) InChI = 1S/C25H14Cl2O5/c26-18-9-13-5-1-3-7-16(13)20-21-17-8-4-2-6-14(17)10-19(27)23(21)25(30)32-12-15(28)11-31-24(29)22(18)20/h1-10H,11-12H2 InChIKey = FQVCXRGPRMNZCY-UHFFFAOYSA-N (a chiral ketone reagent used for enantioselective olefin epoxidations, kinetic resolution of acyclic secondary allylic silyl ethers) Physical Data: a white solid. Solubility: soluble in most organic solvents, such as CH2Cl2, CHCl3, CH3CN, DME, and ethyl acetate. Analysis of Reagent Purity: IR, 1H NMR, 13C NMR, HRMS, and chiral HPLC. Preparative Methods: Direct Synthesis Approach2 (eq 1): (1) Preparation of (R)-1 involves the chlorination of (R)-1,1-binaphthyl-2,2-dicarboxylic acid with sec-BuLi and hexachloroethane. Condensation of the resulting dichorinated product with 3-chloro-2-chloromethyl-1-propene, followed by oxidative cleavage of the olefin moiety with ruthenium trichlorde3 affords (R)-1 in modest yields. Enzymatic Resolution Approach4 (eq 2): (2) Ketone (R)-1 can also be obtained by enzymatic resolution of racemic acetate (±)-2, which is prepared by reduction and acetylation of racemic (±)-1 (prepared according to the direct synthesis approach). Oxidation of the resulting (R)-alcohol affords (R)-1 in high enantioselectivity (> 99% ee). This method has been employed for large-scale synthesis of (R)-1. Purification: silica gel flash column chromatography (30% ethyl acetate in n-hexane). Handling, Storage, and Precautions: very stable at room temperature in air." @default.
- W4234729795 created "2022-05-12" @default.
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- W4234729795 date "2003-10-15" @default.
- W4234729795 modified "2023-09-27" @default.
- W4234729795 title "(R)-2,10-Dichloro-5H-dinaphtho[2,1-g: 1,2-i][1,5]dioxacycloundecin-3,6,9(7H)-trione" @default.
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- W4234729795 doi "https://doi.org/10.1002/047084289x.rn00253" @default.
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