Asymmetric Iodolactonization Using a Trinuclear Zinc Complex Prepared from Bisaminoiminobinaphthol Ligand
General procedure of the enantioselective iodolactonization: A mixture of
1 (0.001 mmol) and Zn(OAc)
2 (0.003 mmol) is stirred for 0.5 hour in anhydrous dichloromethane (1.0 mL) at rt. After cooling the mixture to -78 °C, carboxylic acid (0.1 mmol) in toluene (3.0 mL) is slowly added to the resulting yellow solution and stirred for 0.5 hour at the same temperature. Then,
N-iodosuccinimide (NIS) (24.6 mg, 0.11 mmol) and
I2 (5.0 mg, 0.02 mmol) are added to the reaction mixture. After being stirred for appropriate time, the reaction mixture is quenched with saturated Na
2SO
3 aq. and 1
N NaOH aq., and then the products are extracted with dichloromethane 3 times. The collected organic layer is dried over Na
2SO
4. After removal of the solvent under reduced pressure, the residue is purified by silica-gel column chromatography (hexane/acetone=8/1) to afford the iodolactone.