Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.
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.
Department of Chemistry, 232 Choppin Hall, Louisiana State University, Baton Rouge, LA 70803, USA. rkartika@lsu.edu.
Andrés
A
Villalpando
Mirza A
MA
Saputra
Thomas H
TH
Tugwell
Rendy
R
Kartika
D000438:Alcohols / Q000737:chemistry*; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010705:Phosgene / Q000031:analogs & derivatives* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D006843:Hydrocarbons, Chlorinated; D011725:Pyridines; D010705:Phosgene; C111044:bis(trichloromethyl) carbonate; C023666:pyridine