Lewis Acid-Promoted Cyclization/Halogenation of Allenyl Ethenetricarboxylates and the Amides: Stereoselective Synthesis of Haloalkenyl Five-membered Heterocycles
Lewis Acid-Promoted Cyclization/Halogenation of Allenyl Ethenetricarboxylates and the Amides: Stereoselective Synthesis of Haloalkenyl Five-membered Heterocycles
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路易斯酸促进烯基乙烯三羧酸酯和酰胺的环化/卤化：卤代烯基五元杂环的立体选择性合成
DOI：
10.1039/c4ob00233d
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
A.
中科院分区：
文献类型：
--
作者：
Fukushima;Y.; Yamazaki;S.; Ogawa;A.
本文研究了刘易斯酸促进的乙烯三羧酸丙二烯酯与相应酰胺的分子内反应。乙烯三羧酸丙二烯酯及其酰胺与刘易斯酸如AlCl_3、AlBr_3和ZnX_2（X = Cl、Br、I）反应，立体选择性地生成3，4-反式卤烯基五元杂环。通过NOE实验和环化产物的还原确定立体化学。还进行了卤代烯基官能化的环状化合物的各种转化。
Lewis acid-promoted intramolecular reactions of allenyl ethenetricarboxylates and the corresponding amides have been examined. Reactions of allenyl ethenetricarboxylates and the amides with Lewis acids such as AlCl3, AlBr3 and ZnX2 (X = Cl, Br, I) gave 3,4-trans haloalkenyl five-membered heterocycles stereoselectively. The stereochemistry was determined by NOE experiments and reduction of the cyclized products. Various transformations of the haloalkenyl functionalized cyclic compounds have also been performed.