71434-57-6Relevant academic research and scientific papers
Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
Aretz, Christopher D.,Escobedo, Humberto,Cowen, Bryan J.
supporting information, p. 1880 - 1884 (2018/05/09)
Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.
Diastereoselective C?H Bond Amination for Disubstituted Pyrrolidines
Iovan, Diana A.,Wilding, Matthew J. T.,Baek, Yunjung,Hennessy, Elisabeth T.,Betley, Theodore A.
supporting information, p. 15599 - 15602 (2017/11/16)
We report herein the improved diastereoselective synthesis of 2,5-disubstituted pyrrolidines from aliphatic azides. Experimental and theoretical studies of the C?H amination reaction mediated by the iron dipyrrinato complex (AdL)FeCl(OEt2) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. Among the iron alkoxide and aryloxide catalysts evaluated, the iron phenoxide complex exhibited superior performance towards the generation of syn 2,5-disubstituted pyrrolidines with high diastereoselectivity.
Anti-Markovnikov Hydrofunctionalization of Alkenes: Use of a Benzyl Group as a Traceless Redox-Active Hydrogen Donor
Lonca, Geoffroy Hervé,Ong, Derek Yiren,Tran, Thi Mai Huong,Tejo, Ciputra,Chiba, Shunsuke,Gagosz, Fabien
supporting information, p. 11440 - 11444 (2017/09/11)
A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3- or N3-containing hyp
Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds
Motiwala, Hashim F.,Guelgeze, Belgin,Aube, Jeffrey
experimental part, p. 7005 - 7022 (2012/10/08)
The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.
