Catalytic and Stereoselective Iodination of Prochiral C—H Bonds.

Oxazolines were employed as cyclic chiral directing groups for stereoselective C–H activation. Oxazoline-directed cleavage of the β-C–H bonds followed by reaction with I2 gave a wide range of iodinated products. A large range of functional groups are tolerated. PdI2 was isolated in the reaction and found to be converted to Pd(OAc)2 upon treatment with a combination of I2 and PhI(OAc)2 in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C–H bonds were also investigated.