Dimethyl malonate → HCID 10082482, 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), 194 μL (2.0 mmol) of 2-cyclohexenone, 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 443 mg (97% yield) of the title compound. The optical rotation [α]D23 was +3.45 (c 2.44, CHCl3). The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane:2-propanol=85:15, flow rate 0.5 mL/min, detection at 210 nm) and it was found to be 98% ee.

Provenance & Evidence