(2S)-4-phenylbut-3-en-2-ol

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

Procedure: The product was prepared by General procedure M using 4.5 mg (0.012 mmol) ligand 2, 0.30 mL (0.60 mmol, 2.0 M in hexanes) Me2Zn, 116 μL (0.30 mmol) Ti(OtBu)4, and 19 μL (0.15 mmol) cis-cinnamaldehyde. The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 91% yield (20 mg, 0.14 mmol). 1H NMR (CDCl3, 500 MHz) δ. □ □□ (d, 3H, J=6.2 Hz), 1.66 (br s, 1H), 4.69 (dq, 1H, J=8.5, 6.4 Hz), 5.60 (dd, 1H, J=11.5, 9.3 Hz), 6.40 (d, 1H, J=11.6 Hz), 7.18 (d, 2H, J=7.4 Hz), and 7.25 (t, 3H, J=7.5 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz) δ.23.6, 64.1, 127.2, 128.3, 128.8, 130.0, 135.7, and 136.7 ppm; 1H NMR and 13C NMR spectra for this compound compare with previously reported literature data. The product was prepared by General procedure M The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction solution was cooled to -78° C., added with a dry ether (5 ml) solution of benzylideneacetone (439 mg, 3 mmol) and reacted under stirring at the same temperature for 3 hours. After completion of the reaction, 1 N hydrochloric acid (42 ml) was added to separate the ether layer and the ether layer was washed with 1% hydrochloric acid (20 ml×2) and a saturated saline solution (20 ml×3), dried with anydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain (S)(-)-benzylideneisopropanol. Yield: 435 mg (98%), [α]D20 =24.2° (C=5.16, CHCl3), optical purity: 98%. reacted was added to separate the ether layer the ether layer was washed with 1% hydrochloric acid (20 ml×2) a saturated saline solution (20 ml×3), dried with anydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction solution was cooled to -78° C., added with a dry ether (5 ml) solution of benzylideneacetone (439 mg, 3 mmol) and reacted under stirring at the same temperature for 3 hours. After completion of the reaction, 1 N hydrochloric acid (42 ml) was added to separate the ether layer and the ether layer was washed with 1% hydrochloric acid (20 ml×2) and a saturated saline solution (20 ml×3), dried with anydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain (S)(-)-benzylideneisopropanol. Yield: 435 mg (98%), [α]D20 =24.2° (C=5.16, CHCl3), optical purity: 98%. reacted was added to separate the ether layer the ether layer was washed with 1% hydrochloric acid (20 ml×2) a saturated saline solution (20 ml×3), dried with anydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure

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

Procedure: The product was prepared by General procedure M using 4.5 mg (0.012 mmol) ligand 2, 0.30 mL (0.60 mmol, 2.0 M in hexanes) Me2Zn, 116 μL (0.30 mmol) Ti(OtBu)4, and 19 μL (0.15 mmol) cis-cinnamaldehyde. The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 91% yield (20 mg, 0.14 mmol). 1H NMR (CDCl3, 500 MHz) δ. □ □□ (d, 3H, J=6.2 Hz), 1.66 (br s, 1H), 4.69 (dq, 1H, J=8.5, 6.4 Hz), 5.60 (dd, 1H, J=11.5, 9.3 Hz), 6.40 (d, 1H, J=11.6 Hz), 7.18 (d, 2H, J=7.4 Hz), and 7.25 (t, 3H, J=7.5 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz) δ.23.6, 64.1, 127.2, 128.3, 128.8, 130.0, 135.7, and 136.7 ppm; 1H NMR and 13C NMR spectra for this compound compare with previously reported literature data. The product was prepared by General procedure M The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes)