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Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

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.

SUBMITTER: Villalpando A

PROVIDER: S-EPMC4599979 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

Villalpando Andrés A Saputra Mirza A MA Tugwell Thomas H TH Kartika Rendy R

Chemical communications (Cambridge, England) 20151001 81

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. ...[more]

PMID: 26323232

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