2-Cyclopenten-1-one → HCID 10376463, compound

HRID 916304Notes

Reaction equation

[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH3:7][CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10]>C1(C)C=CC=CC=1>[CH3:12][O:11][C:9]([C:8]([CH:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)([C:13]([O:15][CH3:16])=[O:14])[CH3:7])=[O:10]

Participants

Conditions

Temperature: 30 °C

Procedure

Under an atmosphere of argon, 11.0 mg (0.02 mmol, S/C=50) of Ru[(S,S)-Msdpen] (hexamethylbenzene), 84 μL (1.0 mmol) of 2-cyclopentenone, 133 μL (1.0 mmol) of dimethyl methylmalonate, and 1 mL of toluene were placed in a 20 mL Schlenk tube and stirred at 30° C. for 48 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 116 mg (51% yield) of the title compound. The optical rotation [α]D25 was +87.2(c 1.00, CHCl3). The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=80:20, flow rate 1.5 mL/min, detection at 210 nm) and it was found to be 97% ee.

Workup

customThis solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)

Sources & evidence

ORD record: ord-111fb0cffbd54558926b3aa7546307b5
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268250B2

Reaction notes

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