Methanesulfonamide → HCID 46838210, compound

Participants

Reaction Steps

Compound 10i was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(naphthalen-2-yl)prop-1-enyloxy)dimethylsilane, (9i, 4.7 g, 0.016 mol), AD-mix-β (22.0 g), and CH3SO2NH2 (1.55 g, 0.016 mol) in tert-butyl alcohol-water (60 mL:60 mL). The reaction was quenched with sodium sulfite (15.7 g). After purification by column chromatography on silica gel, 2.5 g (80%) of the desired product was isolated: [α]20D +115° (c 0.7, CHCl3); 1H NMR (CDCl3) δ 8.44 (s, 1H), 8.01-7.86-8.00 (m, 4H), 7.69-7.54 (m, 2H), 5.37-5.27 (m, 1H), 3.86 (d, 1H, J=6.5 Hz), 1.52 (d, 3H, J=7.0 Hz); 13C NMR (CDCl3) δ 202.3, 136.0, 132.4, 130.7, 130.5, 129.7, 129.0, 128.8, 127.9, 127.1, 124.0, 69.4, 22.5. C13H12O2.

Provenance & Evidence