Organohalogenite-Catalyzed Spiroketalization: Enantioselective Synthesis of Bisbenzannulated Spiroketal Cores

Organohalogenite-Catalyzed Spiroketalization: Enantioselective Synthesis of Bisbenzannulated Spiroketal Cores
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DOI:
10.1002/adsc.201500390
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发表时间:
2016-02
影响因子:
5.4
通讯作者:
Jijun Xue;Hongrui Zhang;T. Tian;Keshu Yin;Dongxue Liu;Xianxing Jiang;Ying Li;Xiaojie Jin;X. Yao
Jijun Xue;Hongrui Zhang;T. Tian;Keshu Yin;Dongxue Liu;Xianxing Jiang;Ying Li;Xiaojie Jin;X. Yao
中科院分区:
化学2区
文献类型:
--
作者:
Jijun Xue;Hongrui Zhang;T. Tian;Keshu Yin;Dongxue Liu;Xianxing Jiang;Ying Li;Xiaojie Jin;X. Yao

文献摘要

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一种新的核心结构驱动的策略,分子内芳香族螺缩酮化过程中发现,并用于对映选择性合成bisbenzannulated螺缩酮,生物活性的核心红霉素,具有高水平的对映选择性(高达98%ee)通过有机卤化物介导的不对称分子内芳香族螺缩酮化。这是第一个有机催化的方法,用于建设光学纯bisbenzannulated螺缩酮。
A new core structure-motivated strategy for the intramolecular aromatic spiroketalization process was found and used for the enantioselective synthesis of bisbenzannulated spiroketals, the bioactive core of rubromycins, with high levels of enantioselectivity (up to 98% ee) via an organohalogenite-mediated asymmetric intramolecular aromatic spiroketalization. This is the first organocatalytic method for the construction of optically pure bisbenzannulated spiroketals.