ethyl (3R)-3-hydroxyhexanoate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (2.28 g, 20.63 mmol) in THF (20 mL) cooled to 0° C. is added n-butyllithium (20.63 mmol, 2.5 M in hexanes) and the resulting solution is stirred at 0° C. or 0.5 h. The reaction mixture is cooled to −50° C. followed by slow addition of ethyl (3R)-3-hydroxyhexanoate (1.5 g, 9.38 mmol). After 0.5 h a solution of cinnamyl bromide (2.67 g, 14.06 mmol) in HMPA (2 mL) is added and the reaction mixture is allowed to warm to −20° C. and stirred for 16 h. The reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution, is poured into 20 mL of 1 N hydrochloric acid, and is extracted with two 50-mL portions of EtOAc. The combined organic layers are dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 25% EtOAc-hexanes) to afford ethyl (2R,3R)-2-[(2E)-3-phenyl-2-propen-1-yl]-3-hydroxyhexanoate as a yellow oil (1.82 g, 70% yield). The reaction mixture is cooled to −50° C. to warm to −20° C. stirred for 16 h The reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution is poured into 20 mL of 1 N hydrochloric acid is extracted with two 50-mL portions of EtOAc The combined organic layers are dried over magnesium sulfate concentrated in vacuo purified by silica gel chromatography (elution with 25% EtOAc-hexanes)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (2.28 g, 20.63 mmol) in THF (20 mL) cooled to 0° C. is added n-butyllithium (20.63 mmol, 2.5 M in hexanes) and the resulting solution is stirred at 0° C. or 0.5 h. The reaction mixture is cooled to −50° C. followed by slow addition of ethyl (3R)-3-hydroxyhexanoate (1.5 g, 9.38 mmol). After 0.5 h a solution of cinnamyl bromide (2.67 g, 14.06 mmol) in HMPA (2 mL) is added and the reaction mixture is allowed to warm to −20° C. and stirred for 16 h. The reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution, is poured into 20 mL of 1 N hydrochloric acid, and is extracted with two 50-mL portions of EtOAc. The combined organic layers are dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 25% EtOAc-hexanes) to afford ethyl (2R,3R)-2-[(2E)-3-phenyl-2-propen-1-yl]-3-hydroxyhexanoate as a yellow oil (1.82 g, 70% yield). The reaction mixture is cooled to −50° C. to warm to −20° C. stirred for 16 h The reaction mixture is quenched by addition 3 mL of saturated aqueous ammonium chloride solution is poured into 20 mL of 1 N hydrochloric acid is extracted with two 50-mL portions of EtOAc The combined organic layers are dried over magnesium sulfate concentrated in vacuo purified by silica gel chromatography (elution with 25% EtOAc-hexanes)