Diethyl Malonate → HCID 11776499, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 24.0 mg (0.04 mmol, S/C=50) of RuH[(R,R)-Tsdpen] (1,3,5-trimethylbenzene), 168 μL (2.0 mmol) of 2-cyclopentenone, 304 μL (2.0 mmol) of diethyl malonate, and 2 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 462 mg (95% yield) of the title compound. After this was converted into an ethylene ketal derivative by the same procedure as in Example 3, the optical purity was measured by HPLC (CHIRALCEL OD manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=97: 3, flow rate 0.5 mL/min, detection at 210 nm) and it was found to be 91% ee.

Provenance & Evidence