2-Vinylnaphthalene → (R)-(2-Hydroxy-1-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

Sodium hydroxide (1.89 g, 16 mmol) was dissolved in water (115 mL) and 5.4 mL of this solution was used to dissolve potassium osmium (VI) oxide dihydrate (240 mg) to get a purple suspension. The rest of the sodium hydroxide solution was treated with t-butyl carbamate (5.580 g, 47.1 mmol) in n-propanol (54 mL), followed by addition of t-butyl hypochlorite (5.4 mL, 47.1 mmol). This solution was stirred for 5 min, then hydroquinidine 1,4-phthalazinediyl diether (630 mg) in n-propanol (54 mL) was added, followed by a solution of 2-vinylnaphthalene (2.5 g, 16 mmol) in n-propanol (54 mL) and a solution of potassium osmium (VI) oxide dihydrate previously made. The reaction mixture was stirred at room temperature for 0.5 hr. The reaction mixture was quenched with saturated NaHSO3 solution. After concentration, the residue was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, concentrated under vacuum. The crude product was purified by flash chromatography with 20% ethyl acetate in hexanes to give the title compound (2.6 g) as a solid.

Provenance & Evidence