Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles
Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles
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DOI：
10.1021/acs.orglett.1c02412
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发表时间：
2021-08-30
期刊：
影响因子：
5.2
通讯作者：
Taylor, Mark S.
中科院分区：
文献类型：
--
作者：
Desai, Shrey P.;Taylor, Mark S.
本文介绍了一种3，4-和2，3-环氧醇的区域选择性开环方法。使用二芳基硼酸催化剂，在常规条件下表现出低区域选择性的亲核和亲电伙伴的偶联中，单一的区域异构体是受欢迎的。该方法提供了获得具有立体化学定义的官能化的烷基取代基的芳香族杂环，该产品类别在结构上类似于药物相关化合物，例如无环核苷类似物。
A method for regioselective ring openings of 3,4- and 2,3-epoxy alcohols with ambident nitrogen heterocycles is described. Using a diarylborinic acid catalyst, a single regioisomer is favored in couplings of nucleophile and electrophile partners that display low regioselectivity under conventional conditions. The method provides access to aromatic heterocycles bearing stereochemically defined, functionalized alkyl substituents, a product class similar in structure to medicinally relevant compounds such as the acyclic nucleoside analogues.