Dimethyl methylmalonate → Methyl 2-methoxycarbonyl-2-methyl-4-nitro-3-phenylbutanoate

Participants

Reaction Conditions

Reaction Steps

[(S,S)-N-(pentamethylbenzenesulfonyl)-1,2-diphenyl-ethylenediamine](hexamethylbenzene)ruthenium (13.7 mg, 0.02 mmol, S/C=50), trans-β-nitrostyrene (149 mg, 1.0 mmol), dimethyl methylmalonate (160 μl, 1.2 mmol) and toluene (1 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at −20° C. for 48 hours. The reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2), showing that the isolation yield of the product was 94%. The optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=95:5, flow rate 0.5 m/min, detection by 210 nm), resulting to 97% ee.

Provenance & Evidence