(3aS,4S,6aR)-2,2-Dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol → 2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Participants

Reaction Steps

(3aS,4S,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (1-1) (3 g, 19.2 mmol, 1 equiv) was dissolved in DCM (96 mL) and PS-IBX (32 g, 1.2 mmol/g loading, 2 equiv) was added. The mixture was rotated for 3 days at ambient temperature. Upon disappearance of starting material, the resin was filtered off washing with DCM (3×50 mL). The filtrate was concentrated to afford 3aR,6aR)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-1) as a tan solid. 1H NMR (500 MHz, CDCl3): δ 7.61 (dd, J=5.5, 2.5 Hz, 1H); 6.21 (d, J=6.0 Hz, 1H); 5.27 (dd, J=5.5, 2.5 Hz, 1H); 4.46 (d, J=5.5 Hz, 1H); 1.41 (d, J=3.0 Hz, 6H).

Provenance & Evidence