98598-96-0Relevant articles and documents
Enantioselective Construction of Dihydropyrido[1,2- a]indoles via Organocatalytic Arylmethylation of 2-Enals with Inert Aryl Methane Nucleophiles
Ding, Xiang-Feng,Yang, Wu-Lin,Mao, Jia,Cao, Cong-Xian,Deng, Wei-Ping
, p. 5514 - 5518 (2019)
An organocatalytic asymmetric arylmethylation/N-hemiacetalization of 2-indolyl methane derivatives and 2-enals was developed. Notably, the 2-methyl of indole was readily deprotonated to produce highly reactive nucleophilic species by introducing the nitro
Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans
Andries-Ulmer, Anna,Brunner, Christoph,Rehbein, Julia,Gulder, Tanja
supporting information, p. 13034 - 13041 (2018/09/27)
Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.
Palladium-catalyzed diastereoselective oxyarylation of 2-alkylindoles
Ramella, Vincenzo,He, Zhiheng,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 664 - 667 (2015/03/05)
Diastereoselective oxyarylation of N-protected 2-alkylindoles with commercially available boronic acids and TEMPO as a mild oxidant to give N-protected 2-aryl-2-alkyl-3-(2-chloroacetoxy)indolines is described. Reactions are easy to conduct, and product indolines containing a fully substituted C-center are obtained in good yields with good to excellent selectivities.