Cyclohexane → HCID 68857440, compound

Participants

Reaction Steps

The allylsilane of Example 25 (0.74 g, 4.9 mmol, 1 eq.) was added to a stirring solution of NMO.H2O (2 g, 14.8 mmol, 3 eq.) and OsO4 (100 μL, 0.25 mmol, 0.05 eq.) in acetone (200 mL) and water (50 mL). The reaction was strirred at room temperature overnight before Na2SO3 (0.25 g) was added and the acetone removed in vacuo. The aqueous layer was extracted with EtOAc (3×100 mL) and the combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane:EtOAc, 60:40, RF=0.25) furnished the product as a colourless oil (0.87 g, 4.7 mmol, 95% yield); 1H NMR (400 MHz, CDCl3) 5.56 (1H, m, H-3), 5.50 (1H, m, H-4), 3.94 (1H, m, H-7), 3.81 (1H, m, H-6), 2.35 (1H, m, H-5), 1.86 (1H, m, H-5′), 1.86 (1H, m, H-2), 0.07 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 125.19 (C-4), 120.82 (C-3), 70.39 (C-6), 68.30 (C-7), 35.73 (C-2), 30.16 (C-5), −2.42 (C-1); IR (neat, cm−1) 3423 (b, OH) 1640 (b, C═C) MS (ESI-, m/z) 185.25 [M−H+].

Provenance & Evidence