Allylsilane Reagent-Controlled Divergent Asymmetric Catalytic Reactions of 2-Naphthoquinone-1-methide
Allylsilane Reagent-Controlled Divergent Asymmetric Catalytic Reactions of 2-Naphthoquinone-1-methide
复制标题
烯丙基硅烷试剂控制的 2-萘醌-1-甲基化物的发散不对称催化反应
DOI：
10.1002/chem.202002814
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发表时间：
2020-10-01
影响因子：
4.3
通讯作者：
Li, Can
中科院分区：
文献类型：
--
作者：
Lin, Xiangfeng;Liu, Yan;Li, Can
在Sc-III/Feng配体配合物的催化下，首次报道了烯丙基硅烷试剂控制的2-萘醌-1-甲基（2- napa - q -1-m）的异构不对称Hosomi-Sakurai偶联烯丙基化和杂合diels - alder （HDA）。通过这些方法，在温和的条件下，以直接和高度立体选择性（高达96.5:3.5 e.r）的方式获得了多种独特取代的手性烯丙基功能化二芳基化合物和萘吡喃产物。此外，还证明了2-Nap-Q-1-M可以作为侧不对称Diels-Alder （D-A）反应的有效二烯。这一原理可以直接获得光活性形式的氢苯，它代表了各种天然产物和生物活性分子的结构核心。
Herein, the first allylsilane reagent-controlled divergent asymmetric Hosomi-Sakurai conjugate allylation and hetero-Diels-Alder (HDA) with 2-naphthoquinone-1-methide (2-Nap-Q-1-M) under the catalysis of Sc-III/Feng ligand complex is reported. With these methods, a variety of uniquely substituted chiral allyl-functionalized diaryl compounds and naphthopyran products were obtained in a straightforward and highly stereoselective (up to 96.5:3.5 e.r.) manner under mild conditions. Moreover, it is demonstrated that 2-Nap-Q-1-M can serve as an efficient diene for a side asymmetric Diels-Alder (D-A) reaction. This principle can provide a straightforward access to hydrophenalene in an optically active form, which represents a structural core of various natural products and bioactive molecules.