Benzophenone → (4S,5S)-5-(Acetyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one

Participants

Reaction Steps

A solution containing 1.20 g (7.69 mmol) of compound (2c) and 107 mg (0.587 mmol) benzophenone in 230 mL [1,3]-dioxolane was irradiated at 0° C. for 8.5 hours according to the general procedure. Column chromatography (silica gel 120 g, ethyl acetate in hexanes 50%) gave compound (3c) (1.63 mg. 92%) as a colorless solid, Rf=0.32, [α]25D 36.2°, c 1.3, CHCl3, IR (neat) 1780, 1745, 1216, 759 cm−1; 1H-NMR (500 MHz, CDCl3) δ: 2.08 (s, 3H), 2.52 (dd, 1H, J=10.4 Hz, J=21.7 Hz), 2.61-2.66 (m, 2H), 3.84-3.88 (m, 2H), 3.94-3.98 (m, 2H), 4.09 (dd, 1H, J=5.0 Hz, J=12.3 Hz), 4.32 (dd, 1H, J=2.9 Hz, J=12.3 Hz), 4.62 (mc, 1H), 4.87 (d, 1H, J=3.6 Hz). 13C-NMR (125.8 MHz, CDCl3, Dept) δ: 21.11 (+), 30.16 (−), 40.45 (+), 65.65 (−), 65.78 (−), 65.91 (−), 77.82 (+), 103.54 (+), 170.91 (quat), 175.88 (quat). C10H14O6; Exact Mass: 230.08; Mol. Wt.: 230.21; C, 52.17; H, 6.13; O, 41.70.

Provenance & Evidence