- C-H Activation-Based Traceless Synthesis via Electrophilic Removal of a Directing Group. Rhodium(III)-Catalyzed Entry into Indoles from N-Nitroso and α-Diazo-β-keto Compounds
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A distinct C-H activation-based traceless synthetic protocol via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, N-nitroso-directed C-H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available N-nitroso and α-diazo-β-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the N-nitroso group.
- Wang, Jie,Wang, Mingyang,Chen, Kehao,Zha, Shanke,Song, Chao,Zhu, Jin
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supporting information
p. 1178 - 1181
(2016/03/15)
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- Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine
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Vilsmeier-Haack type cyclizations proved to be particularly efficient for generating parts of the polycyclic cores of many alkaloids, although only monocyclizations have so far been reported. With the goal of rapidly and efficiently constructing polycycli
- Belanger, Guillaume,Larouche-Gauthier, Robin,Menard, Frederic,Nantel, Miguel,Barabe, Francis
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p. 704 - 712
(2007/10/03)
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- Synthesis of Cyclopenta[b]indol-1-ones and Carbazol-4-ones from N-(2-Halophenyl)-Substituted Enaminones by Intramolecular Heck Reaction
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An efficient synthetic route towards N-methylated or nonmethylated 3,4-dihydrocyclopent[b]indol-1(2H)-ones (3) and 1,2,3,9-tetrahydrocarbazol-4(4H)-one (10) was elaborated, based on Pd-catalyzed intramolecular Heck reaction. The chemoselectivity of the cyclization was studied in the case of the bi- and trifunctional substrates 12 and 17, respectively. In the latter case, depending on the catalyst, either the brominated indole 18 or the tetracyclic compound 19 were obtained by single and double Heck reaction, respectively.
- Sorensen, Ulrik S.,Pombo-Villar, Esteban
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- Photocyclization of aryl enaminones. An efficient route to indole alkaloid synthons
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The photocyclization of enaminones was extended to aryl enaminones bearing a substituent on the aromatic moiety.This reaction was studied in order to achieve the synthesis of indole alkaloid synthons.Trials of regioselectivity control were made by using g
- Gardette, Daniel,Gramain, Jean-Claude,Lepage, Marie-Eve,Troin, Yves
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p. 213 - 219
(2007/10/02)
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