Methyl acetoacetate → 3-[(Acetyl) (methoxycarbonyl)methyl]cyclopentanone
Reaktionsgleichung
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]([O:13][CH3:14])(=[O:12])[CH2:8][C:9]([CH3:11])=[O:10]>CC(O)(C)C>[C:9]([CH:8]([C:7]([O:13][CH3:14])=[O:12])[CH:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)(=[O:10])[CH3:11]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
Under an atmosphere of argon, 12.6 mg (0.02 mmol, S/C=50) of Ru[(S,S)-Tsdpen] (hexamethylbenzene), 84 μL (1.0 mmol) of 2-cyclopentenone, 108 μL (1.0 mmol) of methyl acetoacetate, and 1 mL of 2-methyl-2-propanol were placed in a 20 mL Schlenk tube and stirred at 40° C. for 24 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 196 mg (99% yield) of the title compound. The percentage diastereomeric excess and the percentage enantiomeric excess were measured by 1H NMR and HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=80:20, flow rate 1.0 mL/min, detection at 210 nm), it was found that the product was a 1:1 diastereomeric mixture and each diastereomer was present in 70% ee.
Aufarbeitung
- customThis solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)
Quellen und Nachweise
- ORD-Eintrag
- ord-9a2f7ebd60e94c188ffd09aa398a0741
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07268250B2
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