Vinyl Acetate → (S)-3-Isopropenyl-cyclopent-2-enol

Participants

Reaction Conditions

Reaction Steps

Compound (1a*) (63.9 mg, 0.5146 mmol) was dissolved in anhydrous MTBE (1.7 mL) and lipase PS (20 w %, 12.9 mg) and vinyl acetate (31 μL, 0.3363 mmol) were added before the resulting mixture was heated to 40° C. for 18 hours. Solids were removed by filtration and the filtrate concentrated in vacuo. Purification by chromatography (hexane/EtOAc 10/1 to 5/1 to 3/1 to 1/1) using Merck aluminium oxide 90 (0.063-0.200 mm, 70-230 mesh) furnished 25.7 mg of compound 7a as white solid with 40% yield and 43.4 mg of the enantioenriched acetic acid (R)-3-isopropenyl-cyclopent-2-enyl ester as slightly yellow oil with 51% yield.

Provenance & Evidence