Dimethyl malonate → HCID 10081946, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 12.0 mg (0.02 mmol, S/C=50) of RuH[(R,R)-Tsdpen] (1,3,5-trimethylbenzene), 84 μL (1.0 mmol) of 2-cyclopentenone, 114 μL (1.0 mmol) of dimethyl malonate, and 1 mL of acetone 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 213 mg (99% yield) of the title compound. 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 89% ee.

Provenance & Evidence