ON THE STEREOSELECTIVITY IN BISDIHYDROXYLATION OF 1,5-CYCLOOCTADIENE WITH OSMIUM TETROXIDE

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• Toa mixture of OsO4 (7 mg, 0.03 mmol), NMO (6.2 mmol),water (2.4 mL), and acetone (1.2 mL) was added 1 (324 mg, 3.0 mmol). The mixturewas stirred at room temperature for 12 h. After addition of sat.Na2SO3aq,the mixture was evaporated and the residue was chromatographed over silicagel (eluent: water-ethanol-ethyl acetate (1:2:5)) to afford syn-2 as whitecrystals; mp 176–178°C (lit.5 171–173°C);IR (KBr): νO-H 3384 cm−1; 1HNMR (270 MHz, DMSO-d6, 295 K): δ 4.19 (4H, brs, OH), 3.57 (4H, m, CH),1.86 (4H, m, CH 2),1.36 (86 (4H, m, CH2)); 13CNMR (270 MHz, DMSO-d6, 295 K): δ 71.9, 26.8
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• Crystaldata for syn-2: C8H16O4,M = 176.21, tetragonal, space group I41cd(#110), a = 22.520(6), b = 7.030(4)Å, V = 3565(2)Å3,Z = 16, ρ calcd = 1.313 g cm−3, F(000)= 1536.00, 2θmax = 55.1°, MoKα (1 = 0.71069Å), μ(MoKα)= 1.04 cm−1; A total of 1215reflections were collected at 296± 1K on a Rigaku AFC5R diffractometerwith graphite monochromated Mo-Kα radiation and a rotating anode generator.The structure was solved by direct methods (SIR 92) and refined with 768 reflections(I >3.00 σ (I)) and 109 variable parameters; GOF = 1.03, R = 0.052,Rw = 0.054. Atomic coordinates, bond lengths and angles, and thermal parametershave been deposited at Cambridge Crystallographic Center (CCDC). Any requestto the CCDC for this material should quote the full literature citation andthe reference number No. 9/00846B
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• Thisproposed scheme is simplified for clarity, and the most notable omissionsare the various fast equilibria involving association and dissociation ofthe ligand with osmium complexes
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