Diethyl Malonate → HCID 10377693, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 24.0 mg (0.04 mmol, S/C=50) of Ru[(S,S)-Tsdpen](p-cymene), 194 μL (2.0 mmol) of 2-cyclohexenone, 304 μL (2.0 mmol) of diethyl malonate, and 2 mL of 2-methyl-2-propanol 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 409 mg (80% yield) of the title compound. After this was converted into an ethylene ketal derivative as shown 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 61% ee.

Provenance & Evidence