39551-07-0Relevant articles and documents
Alkene Oxyamination Using Malonoyl Peroxides: Preparation of Pyrrolidines and Isoxazolidines
Alamillo-Ferrer, Carla,Curle, Jonathan M.,Davidson, Stuart C.,Lucas, Simon C. C.,Atkinson, Stephen J.,Campbell, Matthew,Kennedy, Alan R.,Tomkinson, Nicholas C. O.
, p. 6728 - 6740 (2018)
Treatment of homoallylic N-tosyl amines or allylic N-tosyl hydroxylamines with 1.5 equiv of a malonoyl peroxide provides a stereoselective method to access functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50-
Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
He, Jia,Jia, Zizi,Tan, Hongcheng,Luo, Xiaohua,Qiu, Dachuan,Shi, Jiarong,Xu, Hai,Li, Yang
, p. 18513 - 18518 (2019/11/19)
A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.
Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes
Ciesielski, Jennifer,Dequirez, Geoffroy,Retailleau, Pascal,Gandon, Vincent,Dauban, Philippe
supporting information, p. 9338 - 9347 (2016/07/14)
The RhII-catalyzed oxyamination and diamination of alkenes generate 1,2-amino alcohols and 1,2-diamines, respectively, in good to excellent yields and with complete regiocontrol. In the case of diamination, the intramolecular reaction provides
Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins
Leger, Paul R.,Murphy, Rebecca A.,Pushkarskaya, Eugenia,Sarpong, Richmond
, p. 4377 - 4383 (2015/03/14)
Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.
Gold- and silver-catalyzed tandem amination/ring expansion of cyclopropyl methanols with sulfonamides as an expedient route to pyrrolidines
Rao, Weidong,Chan, Philip Wai Hong
body text, p. 10486 - 10495 (2009/10/15)
An efficient synthetic route to pyrrolidines that relies on AuCl/ AgOTf-catalyzed tandem amination/ ring expansion of substituted cyclopropyl methanols with sulfonamides is reported herein. The reactions proceed rapidly at 100 °C with catalyst loadings as low as 2 mol % and produce the pyrrolidine products in yields of 30-95%. The method was shown to be applica ble to a broad range of cyclopropyl methanols, including unactivated ones, and sulfonamide substrates containing electron-withdrawing, electron-donating, and sterically-demanding substitu ents. The mechanism is suggested to involve activation of the alcohol substrate by the AuCl/AgOTf catalyst, followed by ionization of the starting material, which causes ring opening of the cyclopropane moiety and trapping by the sulfonamide nucleophile. The resultant aminated acyclic intermediate undergoes subsequent intramolecular hydroamination to give the pyrrolidine.
Gold(I)-catalyzed domino ring-opening ring-closing hydroamination of methylenecyclopropanes (MCPs) with sulfonamides: Facile preparation of pyrrolidine derivatives
Shi, Min,Liu, Le-Ping,Tang, Jie
, p. 4043 - 4046 (2007/10/03)
Reaction of methylenecyclopropanes 1 with sulfonamides produces the corresponding pyrrolidine derivatives 3 in moderate to good yields under the catalysis of Au(I) via a domino ring-opening ring-closing hydroamination process.
Synthesis of Five- and Six-Membered Nitrogen Heterocycles via a Palladium(II)-Catalyzed Cyclization of Unsaturated Amides
Tamaru, Yoshinao,Hojo, Makoto,Kawamura, Shin-ichi,Yoshida, Zen-ichi
, p. 4089 - 4090 (2007/10/02)
Palladium(II)-catalyzed arylation of N-4-pentenyl-p-toluenesulfonamides 2 with ArSn(n-Bu)3 under oxidative conditions (CuCl2 in ether) provides either 2-arylpiperidines 5 or N-(chloro-5-arylpentyl)-p-toluenesulfonamides 6 depending on the kind of arylatin
