Dimethyl malonate → HCID 10398317, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 11.0 mg (0.02 mmol, S/C=100) of Ru[(S,S)-Msdpen] (hexamethylbenzene), 168 μL (2.0 mmol) of 2-cyclopentenone, 228 μl (2.0 mmol) of dimethyl malonate, and 1 mL of 2-methyl-2-propanol were placed in a 20 mL Schlenk tube and stirred at 30° C. for 72 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 425 mg (99% yield) of the title compound. The optical rotation [α]D21 was +96.3 (c 0.54, CHCl3). The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=80:20, flow rate 1.0 mL/min, detection at 210 nm) and it was found to be 98% ee.

Provenance & Evidence