Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols
© The Royal Society of Chemistry. We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.
Publication Source (Journal or Book title)
Villalpando, A., Saputra, M., Tugwell, T., & Kartika, R. (2015). Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols. Chemical Communications, 51 (81), 15075-15078. https://doi.org/10.1039/c5cc06365e