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4. Ex (OsO₄ + NMO)

Alkene to Diol

(OsO₄ + NMO)

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Examples:

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Example 1

To a solution of the SM (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL) and H2O (7.8 mL) at RT was added NMO (2.48 g, 21.16 mmol). After 2 min, OsO4 (4% in H2O, 3.37 mL) was added and the rxn mixture was stirred at RT for 23 h. The mixture was quenched with aq 0.2M Na2S2O3 (25 mL) and extracted with DCM (2 x 50 mL). The combined organics were washed with aq 0.2M Na2S2O3 (10 mL), dried (MgSO4), and concentrated in vacuo. The crude material was purified by flash chromatography (17-100% EtOAc/heptane) to provide the product as a yellow solid. [1.31 g, 57%]

[Patent Reference: WO2016001341, page 126, (9.1 MB)]