光氧化还原诱导的立体选择性去芳构化自由基（4+2）-环化/1,4-加成级联反应用于合成高度官能化的六氢-1H-咔唑。
A Photoredox-Induced Stereoselective Dearomative Radical (4+2)-Cyclization/1,4-Addition Cascade for the Synthesis of Highly Functionalized Hexahydro-1H-carbazoles.
机构信息
Department of Chemistry-Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
Department of Chemistry-Institute of Inorganic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany.
出版信息
Angew Chem Int Ed Engl. 2017 Jan 24;56(5):1402-1406. doi: 10.1002/anie.201610974. Epub 2017 Jan 9.
A stereoselective synthesis of functionalized hexahydrocarbazoles was developed based on an unprecedented photoredox-induced dearomative radical (4+2)-cyclization/1,4-addition cascade between 3-(2-iodoethyl)indoles and acceptor-substituted alkenes. The title reaction simultaneously generates three C-C bonds and one C-H bond, along with three contiguous stereogenic centers. The hexahydro-1H-carbazole products are highly valuable intermediates for the synthesis of novel antibiotics, as well as unnatural ring homologues of polycyclic indoline alkaloids.
发展了一种基于前所未有的光氧化还原诱导去芳构化自由基（4+2）-环化/1,4-加成级联反应的功能化六氢咔唑的立体选择性合成，该反应在 3-(2-碘乙基)吲哚和取代的烯烃受体之间进行。该标题反应同时生成三个 C-C 键和一个 C-H 键，以及三个连续的立体中心。六氢-1H-咔唑产物是合成新型抗生素以及多环吲哚生物碱的非天然环同系物的非常有价值的中间体。
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