40899-73-8Relevant articles and documents
Enantioselective Synthesis of Pyrrolizin-1-ones via Lewis Base Catalyzed N-Allylation of N-Silyl Pyrrole Latent Nucleophiles
Lange, Markus,Zi, You,Vilotijevic, Ivan
, p. 1259 - 1269 (2020)
Pyrrolizidine alkaloids and their derivatives often feature interesting biological activities. A class of substituted 2,3-dihydro-1H-pyrrolizin-1-one derivatives has been explored as a potential treatment for Alzheimer's disease, but enantioselective synthesis of these molecules is still elusive. We report that enantioselective N-allylation of N-silyl pyrrole latent nucleophiles with allylic fluorides followed by hydrogenation and diastereoselective Friedel-Crafts cyclization constitute an efficient synthetic route to access enantioenriched substituted 2,3-dihydro-1H-pyrrolizin-1-ones.
Electron transfer-induced reduction of organic halides with amines
Fukuyama, Takahide,Fujita, Yuki,Miyoshi, Hayato,Ryu, Ilhyong,Kao, Shih-Chieh,Wu, Yen-Ku
supporting information, p. 5582 - 5585 (2018/06/04)
Reduction of a variety of organo halides was examined by using amines as a sacrificial hydrogen source. UV light-induced reduction of vinyl and aryl halides with triethylamine proceeded smoothly to give the corresponding reduced products. High temperature heating also caused the reduction and DABCO (1,4-diazabicyclo[2.2.2]octane) also served as a good reducing reagent.
Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents
Grenet, Erwann,Das, Ashis,Caramenti, Paola,Waser, Jér?me
supporting information, p. 1208 - 1214 (2018/06/04)
The C–H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C–H bond in bipyridinones and quinoline N-oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline N-oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups.