路易斯酸催化的烯酮连接的环己二烯酮的组合非对映选择性卤化级联环化反应
Combined Lewis Acid Catalyzed Diastereoselective Halogenative Cascade Annulation of Enone-Tethered Cyclohexadienones.
作者信息
Nallamilli Tarun, Munakala Anandarao, Chegondi Rambabu
机构信息
Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
出版信息
Org Lett. 2023 Nov 24;25(46):8240-8245. doi: 10.1021/acs.orglett.3c03269. Epub 2023 Nov 10.
The cascade difunctionalization of -unsaturated carbonyls by nucleophilic halogenation followed by enolate trapping with other electrophiles is highly challenging in synthetic organic chemistry. Herein, we report a chemo- and diastereoselective cascade annulation of enone-tethered cyclohexadienones by using an unconventional combined Lewis acid catalyzed halogenation reaction in the presence of an In(III)-catalyst and trimethylsilyl halide. The reaction provides highly functionalized bicyclic enones with four contiguous stereocenters.
在合成有机化学中，通过亲核卤化接着用其他亲电试剂捕获烯醇盐来实现α,β-不饱和羰基化合物的串联双官能化极具挑战性。在此，我们报道了一种烯酮连接的环己二烯酮的化学和非对映选择性串联环化反应，该反应使用了一种非常规的组合，即在In(III)催化剂和三甲基硅基卤化物存在下的路易斯酸催化卤化反应。该反应提供了具有四个相邻立体中心的高度官能化的双环烯酮。
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