Abstract
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 types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alcohols / chemistry*
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Halogenation
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Hydrocarbons, Chlorinated / chemical synthesis*
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Hydrocarbons, Chlorinated / chemistry
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Molecular Conformation
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Phosgene / analogs & derivatives*
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Phosgene / chemistry
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Pyridines / chemistry*
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Stereoisomerism
Substances
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Alcohols
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Hydrocarbons, Chlorinated
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Pyridines
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Phosgene
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bis(trichloromethyl) carbonate
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pyridine