Methanesulfonamide → (R)-1-(3-bromophenyl)-2-hydroxypropan-1-one

Participants

Reaction Steps

Compound 10d was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-bromophenyl)prop-1-enyloxy)dimethylsilane, (9d, 1.15 g, 0.0035 mol), AD-mix-β (4.9 g), and CH3SO2NH2 (334 mg, 3.5 mmol) in tert-butyl alcohol-water (17.5 mL. 17.5 mL). The reaction was quenched with sodium sulfite (3.5 g). After purification by column chromatography on silica gel, 0.700 g (88%) of the desired product was isolated: [α]20D +61.1° (c 1.3, CHCl3); 1H NMR (CDCl3) δ 8.09-8.04 (m, 1H), 7.87-7.81 (m, 1H), 7.78-7.72 (m, 1H), 7.39 (t, 1H, J=8.0 Hz), 5.18-5.05 (m, 1H), 3.66 (d, 1H, J=6.4 Hz), 1.45 (d, 3H, J=7.2 Hz); 13C NMR (CDCl3) δ 201.2, 136.8, 135.2, 131.6, 130.4, 127.1, 123.3, 69.5, 22.1. C9H9BrO2.

Provenance & Evidence