Neighboring Hydroxyl Group-Assisted Allylboration and Lewis Acid-Mediated Carbonyl-Ene Reaction for Access to a Hapalindole Cyclohexane Core with Multiple Contiguous Stereogenic Centers,The Journal of Organic Chemistry

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Neighboring Hydroxyl Group-Assisted Allylboration and Lewis Acid-Mediated Carbonyl-Ene Reaction for Access to a Hapalindole Cyclohexane Core with Multiple Contiguous Stereogenic Centers
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-01-09 00:00:00 , DOI: 10.1021/acs.joc.8b02712
Lu Li ₁ , Zhao Yang ₁ , Jiao Yang ₁ , Quanzheng Zhang ₁ , Qiuyuan Tan ₁ , Changhui Zhang ₁ , Min Zhang ₁

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A neighboring hydroxyl group-assisted allylboration of 3-indolyl ketones with γ,γ-disubstituted allylboronic acids is reported, affording various 3-indolyl-substituted homoallylic alcohols in good yields with excellent diastereoselectivies (up to >20:1 dr). The hydroxyl group not only played a vital role in the challenging allylboration but was elaborated for the subsequent construction of a hapalindole cyclohexane core by a highly diastereoselective Lewis acid-catalyzed carbonyl-ene reaction. In the overall process, four contiguous stereogenic centers including two quaternary stereogenic centers were installed.

中文翻译：

邻近的羟基协助的烯丙基硼化和路易斯酸介导的羰基-烯类反应，可得到具有多个连续立体中心的卤代吲哚环己烷核

据报道，邻位羟基辅助的3-吲哚基酮与γ，γ-二取代的烯丙基硼酸的烯丙基硼酸酯化反应以良好的收率提供了各种3-吲哚基取代的均烯丙基醇，非对映异构选择性极好（高达> 20：1 dr）。羟基不仅在极具挑战性的烯丙基硼化中起着至关重要的作用，而且还通过高度非对映选择性的路易斯酸催化的羰基-烯反应为随后的construction吲哚环己烷核的构建作了详细说明。在整个过程中，安装了四个连续的立体成因中心，包括两个四级立体成因中心。

更新日期：2019-01-09

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