Cerium(III) chloride → (3aS,4R,6aR)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

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Reaction Conditions

Reaction Steps

(3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-2) (1.5 g, 5.4 mmol, 1 equiv) was dissolved in MeOH (54 mL). The solution was cooled to −78° C. and cerium(III) chloride (1.4 g, 5.7 mmol, 1.05 equiv) was added followed by sodium borohydride (216 mg, 5.7 mmol, 1.05 equiv). The resulting mixture was stirred at the same temperature for 5 minutes. Upon disappearance of the starting material, the reaction was quenched with the addition of water (10 mL) and concentrated. The residue was partitioned between EtOAc (100 mL) and water (40 mL), the organics were dried over MgSO4, filtered and concentrated to afford (3aS,4R,6aR)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (5-3) as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 6.31 (s, 1 II); 4.92 (dd, J=5.5, 2.0 Hz, 1H); 4.69 (t, J=5.5 Hz, 1H); 4.41 (dd, J=10.5, 5.5 Hz, 1H); 1.43 (s, 3H); 1.40 (s, 3H).

Provenance & Evidence