Dimethyl malonate → methyl(R)-2-methoxycarbonyl-4-nitro-3-phenylbutanoate

Participants

Reaction Conditions

Reaction Steps

[(S,S)-N-(2,4,6-triisopropylbenzenesulfonyl)-1,2-diphenylethylenediamine](hexamethylbenzene)ruthenium (14.8 mg, 0.02 mmol, S/C=50), trans-β-nitrostyrene (149 mg, 1.0 mmol), dimethyl malonate (114 μl, 1.0 mmol) and toluene (1 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at 0° C. for 60 hours. 1HNMR determination of the solution showed that the yield of the product was 99%. The reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2), and the optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=90:10, flow rate 0.5 ml/min, detection by 210 nm), resulting to 91% ee.

Provenance & Evidence