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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence