2-Cyclohexen-1-one → (R)-3-Phenylcyclohexanone

Participants

Reaction Steps

Cyclohexenone (30 mg, 0.312 mmol), a rhodium complex of Rh(acac) (C2H4)2 (5.2 mg, 0.02 mmol), 50 mg of the polymer having the (R)-BINAP group (17) obtained in Preparation Example 1 and a phenylboronic acid (244 mg, 2.0 mmol) were reacted in 4 mL of water at 100° C. for 13 hours. The reaction mixture was filtered out to recover the polymer having the (R)-BINAP group. Meanwhile, the filtrate was extracted with ether and washed with saturated sodium hydrogen carbonate aqueous solution and saturated saline. It was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative chromatography (hexyane:ethyl acetate=3:1) to obtain 43.5 mg of (R)-3-phenylcyclohexanone with optical purity of 97% ee in 80% yield.

Provenance & Evidence