Triphosgene-pyridine Mediated Stereoselective Chlorination of Acyclic Aliphatic 1,3-diols

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2015 Sep 2

PMID 26323232

Citations 3

Authors

Andres Villalpando

Mirza A Saputra

Thomas H Tugwell

Rendy Kartika

Affiliations

Soon will be listed here.

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.

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