106970-98-3Relevant academic research and scientific papers
Phase-Transfer Catalyzed Asymmetric [4 + 1] Annulations for the Synthesis of Chiral 2,2-Disubstituted Tetrahydrothiophenes
Yin, Qi,Wen, Xiaolu,Chen, Yiwei,Gong, Xiangnan,Hu, Lin
supporting information, p. 7529 - 7534 (2021/10/02)
An efficient catalytic asymmetric [4 + 1] reaction, which features the use of simple β-keto esters as one-carbon nucleophiles and 5-succinimidothio-pent-2-enoates as four-atom bielectrophiles, has been developed in the presence of a bifunctional chiral ph
Urea-Catalyzed Vinyl Carbocation Formation Enables Mild Functionalization of Unactivated C-H Bonds
Bagdasarian, Alex L.,Popov, Stasik,Wigman, Benjamin,Wei, Wenjing,Lee, Woojin,Nelson, Hosea M.
supporting information, p. 7775 - 7779 (2020/07/15)
Herein we report the 3,5-bistrifluoromethylphenyl urea-catalyzed functionalization of unactivated C-H bonds. In this system, the urea catalyst mediates the formation of high-energy vinyl carbocations that undergo facile C-H insertion and Friedel-Crafts re
Synthesis of the 1,3,4-Oxadiazole Core through Thermolysis of Geminal Diazides
Erhardt, Hellmuth,Mohr, Fabian,Kirsch, Stefan F.
supporting information, p. 5629 - 5632 (2016/12/14)
The thermolysis of geminal diazides derived from acylacetate compounds is an efficient tool for the rapid construction of the 1,3,4-oxadiazole core. While a broad range of ethyl esters undergoes smooth transformation to the desired heterocycles that contain the ester moiety in moderate to high yields, the analogous tert-butyl esters give rise to the oxadiazoles with acyl groups, presumably through a pathway of decarboxylation followed by a new acyl transfer.
One-pot Unsymmetrical Ketone Synthesis Employing a Pyrrole-Bearing Formal Carbonyl Dication Linchpin Reagent
Heller, Stephen T.,Newton, James N.,Fu, Tingting,Sarpong, Richmond
supporting information, p. 9839 - 9843 (2015/08/19)
A one-pot procedure for the synthesis of unsymmetrical ketones utilizing a pyrrole-bearing carbonyl linchpin reagent (carbonyl linchpin N,O-dimethylhydroxylamine pyrrole; CLAmP) is reported. In contrast to other carbonyl dielectrophile equivalents, CLAmP enables the synthesis of ketones from a variety of organolithium and Grignard reagents. The electrophilic nature of CLAmP enables the addition of less reactive as well as thermally unstable nucleophiles. CLAmP was designed to form kinetically stable tetrahedral intermediates upon the addition of organometallic nucleophiles. Evidence for the existence of persistent tetrahedral intermediates was obtained through in situ IR studies.
Regioselective synthesis of highly aryl-substituted pyrrole carboxylates as useful medicinal chemistry leads
Bhatt, Ulhas,Duffy, Bryan C.,Guzzo, Peter R.,Cheng, Leifeng,Elebring, Thomas
, p. 2793 - 2806 (2008/02/12)
The regioselective syntheses of two pharmaceutically relevant pyrrole scaffolds are described. A synthetic route for the preparation of differentially substituted pyrrole-3,4-dicarboxylates is presented and exemplified. This route circumvents some of the
