Dimethyl malonate → dimethyl (S)-alpha-(1,3-diphenyl-2-propen-1-yl)malonate

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Reaction Steps

In 0.5 ml of dichloromethane were suspended 0.9 mg (2.5 μmol) of [PdCl(η3-C3H5)]2 and 1.8 mg (5.5 μmol) of (R,R)-t-Bu-QuinoxP* (1), followed by stirring at room temperature for 10 to 30 minutes. To the resulting solution were added a solution of 126 mg (0.50 mmol) of 1,3-diphenyl-2-propenyl acetate in 1.5 ml of dichloromethane, 171 μl (1.50 mmol) of dimethyl malonate, 367 μl (1.50 mmol) of N,O-bis(trimethylsilyl)acetamide (BSA), and a trace amount of potassium acetate. The reaction system was stirred at room temperature for 1 hour. The reaction mixture was diluted with diethyl ether, and a saturated aqueous solution of ammonium chloride was added to stop the reaction. The resulting mixture was extracted with diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. Any volatile matter was evaporated off, and the residue was purified by silica gel column chromatography.

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