布朗斯特酸催化的[2 + 2 + 1]环化反应在四氢吲哚和四氢环戊并[b]吡咯的模块化合成中的应用。
Brønsted Acid-Catalyzed Formal [2 + 2 + 1] Annulation for the Modular Synthesis of Tetrahydroindoles and Tetrahydrocyclopenta[ b]pyrroles.
机构信息
Department of Chemistry , 232 Choppin Hall, Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
出版信息
Org Lett. 2019 May 17;21(10):3610-3614. doi: 10.1021/acs.orglett.9b01032. Epub 2019 Apr 29.
Abstract
An expedient synthesis of tetrahydroindoles and tetrahydrocyclopenta[ b]pyrroles, highlighted by Brønsted acid catalyzed formal [2 + 2 + 1] annulation reaction, is reported. Using three readily accessible reaction components, i.e., an electrophilic species in silyloxyallyl cations and two distinct nucleophiles in silylenol ethers and amines, our chemistry enables the assembly and functionalization of these biologically important N-heterocycles in a highly modular manner.
摘要
本文报道了一种通过 Brønsted 酸催化的形式[2+2+1]环加成反应，高效合成四氢吲哚和四氢环戊[b]吡咯的方法。该方法使用了三种易得的反应组分，即硅氧基烯丙基阳离子中的亲电物种、硅烯醇醚和胺中的两种不同亲核试剂，我们的化学方法能够以高度模块化的方式组装和官能化这些具有重要生物学意义的 N-杂环。
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