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首页> 外文期刊>Synlett >DBU-Promoted Elimination Reactions of Vicinal Dibromoalkanes Mediated by Adjacent O-Functional Groups, and Applications to the Synthesis of Biologically Active Natural Products
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DBU-Promoted Elimination Reactions of Vicinal Dibromoalkanes Mediated by Adjacent O-Functional Groups, and Applications to the Synthesis of Biologically Active Natural Products

机译：DBU促进邻邻O-官能团介导的邻二溴链烷的消除反应及其在生物活性天然产物合成中的应用

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摘要

Regioselective elimination reactions of 1,2-dibromoalkanes possessing aryloxy or acyloxy groups at the C-3 position can be carried out under mild basic conditions to produce the corresponding 2-brorno-1-alkenes. The regioselectivity of these processes is controlled by the acidity enhancement of hydrogens at C-2 caused by the inductive electron-withdrawing effects of substituents at C-3. A similar acidity enhancement; of the hydrogens at C-1 causes selective DBU-promoted, two-step transformations of 1,2-dibromoalkanes to alkyne derivatives. The. 2-bromo-1-alkenes and alkynes, readily prepared using these regioselective elimination reactions, have been employed as key intermediates in the synthesis of biologically active natural products.
机译：可以在温和的碱性条件下进行在C-3位具有芳氧基或酰氧基的1，2-二溴烷烃的区域选择性消除反应，以产生相应的2-溴-1-烯烃。这些过程的区域选择性是由取代基在C-3处的感应吸电子作用引起的C-2处氢的酸度增强控制的。类似的酸度增强; C-1处的氢原子引起选择性DBU促进的1，2-二溴烷烃两步转化为炔烃衍生物。的。使用这些区域选择性消除反应容易制备的2-溴-1-烯烃和炔烃已被用作生物活性天然产物合成中的关键中间体。

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