Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N,N-Dimethylformamide Dimethyl Acetal.,The Journal of Organic Chemistry

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Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N,N-Dimethylformamide Dimethyl Acetal.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-05-01 , DOI: 10.1021/acs.joc.0c00290
Dayong Sang ₁ , Huaxin Yue _{1,

2} , Zhengdong Zhao ₁ , Pengtao Yang ₁ , Juan Tian ₁

Affiliation

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

中文翻译：

三碘化铝和N，N-二甲基甲酰胺二甲基乙缩醛对酸不稳定的芳烷基醚的手性辅助选择性裂解。

N，N-二甲基甲酰胺二甲基乙缩醛（DMF-DMA）利用三碘化铝通过相邻基团的参与选择性裂解醚。包括羧酸盐，烯丙基，叔丁基二甲基甲硅烷基（TBS）和叔丁氧羰基（Boc）在内的各种酸不稳定官能团均完好无损。该方法为裂解邻苯二酚单烷基醚和从乙缩醛型保护基（如甲氧基甲基（MOM），甲氧基乙氧基甲基（MEM）和四氢吡喃基（THP））上化学选择性解吸酚提供了一种有效的方法。

更新日期：2020-04-22

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