Benzcatechinborane → Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

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To a solution of ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate (1.6 g, 2.78 mmol) and (R)-2-methyl-CBS-oxazaborolidine (116 mg, 0.42 mmol) in anhydrous toluene at −40° C. was added a solution of catecholborane (355 μL, 3.34 mmol) in toluene (1.6 mL) over 15 minutes. The reaction mixture was stirred for 1 hour and quenched with sodium carbonate solution, diluted with ethyl acetate and stirred vigorously for 20 minutes at room temperature. The aqueous layer was removed and the organic layer was washed with sodium carbonate solution (4×), saturated ammonium chloride solution, dried, filtered, concentrated in vacuo and purified by flash column chromatography to give the desired product.

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