三光气-吡啶介导的无环脂肪族1,3-二醇的立体选择性氯化反应
Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.
作者信息
Villalpando Andrés, Saputra Mirza A, Tugwell Thomas H, Kartika Rendy
机构信息
Department of Chemistry, 232 Choppin Hall, Louisiana State University, Baton Rouge, LA 70803, USA.
出版信息
Chem Commun (Camb). 2015 Oct 18;51(81):15075-8. doi: 10.1039/c5cc06365e.
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.
摘要
我们描述了一种使用三光气和吡啶的混合物对立体互补的无环脂肪族1,3 - 二醇进行氯化的策略。虽然1,3 - 反式二醇很容易生成1,3 - 反式二氯化物，但1,3 - 顺式二醇必须先转化为1,3 - 顺式二醇单硅醚才能得到相应的1,3 - 顺式二氯化物。这些二氯化反应方案操作简单、条件温和，并且高级合成中间体很容易耐受。
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