63914-70-5Relevant articles and documents
Dihalogenation of Alkenes Using Combinations of N-Halosuccinimides and Alkali Metal Halides
Barrio, Pablo,García-Pedrero, Olaya,López-Matanza, Pablo,Rodríguez, Félix,Rubio-Presa, Rubén
supporting information, p. 4762 - 4766 (2021/09/10)
A simple, efficient and eco-friendly method for the vicinal dihalogenation of alkenes is described. The reaction is performed with a combination of a N-halosuccinimide and an alkali metal halide using environmentally benign solvents such as acetic acid an
Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co–Catalyzed, Enantioselective Proton-Transfer
Metternich, Jan B.,Reiterer, Martin,Jacobsen, Eric N.
supporting information, p. 4092 - 4097 (2020/09/01)
We report an enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C?C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis. (Figure presented.).
Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols
Phipps, Erik J.T.,Rovis, Tomislav
supporting information, p. 6807 - 6811 (2019/05/10)
We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: Directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.