(2R)-2-hydroxy-1-phenylpropan-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 10b was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-phenprop-1-enyloxy)dimethylsilane (9b, 7.2 g, 0.029 mol), AD-mix-β (40.7 g), and CH3SO2NH2 (2.8 g, 0.0294 mol) in tert-butyl alcohol-water (110 mL:110 mL) The reaction was quenched with sodium sulfite (29.1 g). After purification, 2.49 g (80%) of the title product was isolated: [α]20D +84.9° (c 1.6, CHCl3); 1H NMR (CDCl3) δ 7.96-7.90 (m, 2H), 7.66-7.58 (m, 1H), 7.54-7.47 (m, 2H), 5.23-5.12 (m, 1H), 3.84 (d, 1H, J=6.3 Hz), 1.45 (d, 3H, J=7.05 Hz); 13C NMR (CDCl3) δ 202.4, 134.0, 133.4, 128.9, 128.7, 69.3, 22.3. C9H10O2. Compound 10b was synthesized by a procedure similar to was quenched with sodium sulfite (29.1 g) After purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 4b was synthesized by a procedure similar to that described for (2S,3S)-4a using (R)-1-phenyl-2-hydroxypropan-1-one (10b, 3.49 g, 0.0233 mol), Proton sponge (5.9 g), triflic anhydride (4.2 mL, 26 mmol), and 2-amino-2-methyl-1-propanol (4.6 g, 0.052 mol) in CH2Cl2 (50 mL). After purification by chromatography on silica gel, 3.52 g (68%) of the free base 4b was isolated, and converted to 1.19 g of the hemi-D-tartrate salt, which had >99% ee: mp 112-113° C.; [α]20D +15.8° (c 1.1, CH3OH); 1H NMR (methanol-d4) δ 7.61-7.59 (m, 2H), 7.44-7.36 (m, 3H), 4.32 (s, 1H), 4.24 (d, 1H, J=12.3 Hz), 3.58-3.48 (m, 2H), 1.64 (s, 3H), 1.39 (s, 3H), 1.09 (d, 3H, J=6.6 Hz); 13C NMR (methanol-d4) δ 179.1, 142.4, 130.3, 129.6 (2C), 127.9 (2C), 97.3, 75.4, 67.4, 55.47, 55.27, 24.1, 21.3, 14.3; LCMS (ESI) m/z 222.4 (M-tartrate)+; Anal. (C15H22NO5.0.5H2O) calcd: C, 59.00; H, 7.59; N, 4.59. found: C, 58.77; H, 7.46; N, 4.64. Compound 4b was synthesized by a procedure similar to After purification by chromatography on silica gel