1291093-63-4Relevant academic research and scientific papers
Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks
Paptchikhine, Alexander,Itto, Kaori,Andersson, Pher G.
, p. 3989 - 3991 (2011)
A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity. The Royal Society of Chemistry.
Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry
Peters, Byron K.,Rodriguez, Kevin X.,Reisberg, Solomon H.,Beil, Sebastian B.,Kawamata, Yu,Baran, Phil S.,Hickey, David P.,Klunder, Kevin,Gorey, Timothy J.,Anderson, Scott L.,Minteer, Shelley D.,Collins, Michael,Starr, Jeremy,Chen, Longrui,Udyavara, Sagar,Neurock, Matthew
, p. 838 - 845 (2019/04/30)
Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.
Birch reaction followed by asymmetric iridium-catalysed hydrogenation
Cadu, Alban,Paptchikhine, Alexander,Andersson, Pher G.
experimental part, p. 3796 - 3800 (2012/01/06)
Birch reaction products are asymmetrically hydrogenated with high enantio- and diastereoselectivity via iridium catalysts. This new method of producing chiral compounds was explored for a variety of 1,3-di- and 1,2,4-tri-substituted cyclohexadienes. Georg
