Catalytic and stereoselective iodination of prochiral C-H bonds

Oxazo lines were employed,as cyclic chiral directing groups for stereoselective C-H activation. Oxazoline-directed cleavage of the P-C-H bonds followed by reaction with I, 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 I-2 and PhI(OAC)(2) in situ to achieve catalytic turnover. Diastereoselective iodination of prochiral C-H bonds were also investigated. (c) 2005 Elsevier Ltd. All rights reserved.