Diarylborinic Acid-Catalyzed Ring Opening of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides: Synthesis of 1,2,4-Trisubstituted Cyclopentanes,Organic Letters

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Diarylborinic Acid-Catalyzed Ring Opening of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides: Synthesis of 1,2,4-Trisubstituted Cyclopentanes
Organic Letters ( IF 4.9 ) Pub Date : 2023-10-09 , DOI: 10.1021/acs.orglett.3c02886
Shan-Shan Xun ₁ , Han Wang ₂ , Chang-Bin Yu ₂ , Sheng-Mei Lu ₂ , Yong-Gui Zhou ₂

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A diarylborinic acid-catalyzed ring opening of cis-4-hydroxymethyl-1,2-cyclopentene oxides was developed with N-nucleophiles including anilines, benzotriazole, and alkylamines, as well as S-nucleophiles, affording 1,2,4-trisubstituted cyclopentane compounds containing a quaternary carbon center. The mechanism study indicated that the “half-cage” structure formed by the epoxide substrate and the catalyst prevents the nucleophiles from attacking the inner side of the “half-cage”, resulting in the desired ring-opening product.

中文翻译：

二芳基硼酸催化顺式-4-羟甲基-1,2-环戊烯氧化物的开环：1,2,4-三取代环戊烷的合成

使用苯胺、苯并三唑和烷基胺等N亲核试剂以及S亲核试剂开发了二芳基硼酸催化的顺式-4-羟甲基-1,2-环戊烯氧化物开环，得到 1,2,4-三取代环戊烷含有季碳中心的化合物。机理研究表明，环氧化物底物和催化剂形成的“半笼”结构可以防止亲核试剂攻击“半笼”的内侧，从而产生所需的开环产物。

更新日期：2023-10-09

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