Catalytic and stereoselective iodination of prochiral C-H bonds

Ramesh Giri, Xiao Chen, Xue Shi Hao, Jiao Jie Li, Jue Liang, Zi Peng Fan, Jin Quan Yu

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)3502-3505
Number of pages4
JournalTetrahedron Asymmetry
Volume16
Issue number21
DOIs
StatePublished - Oct 31 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Giri, R., Chen, X., Hao, X. S., Li, J. J., Liang, J., Fan, Z. P., & Yu, J. Q. (2005). Catalytic and stereoselective iodination of prochiral C-H bonds. Tetrahedron Asymmetry, 16(21), 3502-3505. https://doi.org/10.1016/j.tetasy.2005.08.049