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

HRID 2055824Notes

Reaction equation

[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[C:12]([O:19][CH3:20])(=[O:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15]>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14]([CH:13]([C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[C:12]([O:19][CH3:20])=[O:18])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

[(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.

Workup

customThe reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2)
customresulting to 91% ee

Sources & evidence

ORD record: ord-565bad6784434e6abc915d4082b93522
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332622B2

Reaction notes

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