1H-imidazole; iodine; triphenylphosphine in diethyl ether; acetonitrile T=0°C; 0.25 h; Yield given;

N-iodo-succinimide; triphenylphosphine in dichloromethane T=-10 - 0°C; optical yield given as percent dediastereoselective reaction;

1: 1.) 75percent tert-butyl hydroperoxide, selenium dioxide; 2.) sodium borohydride / 1.) dichloromethane, rt., 3 h; 2.) methanol, 0 deg C, 10 min 2: Ph3P, imidazole, I2 / acetonitrile; diethyl ether / 0 deg C, 5 min then rt., 0.5 h View Scheme