269071-95-6Relevant articles and documents
Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids
Wommack, Andrew J.,Kingsbury, Jason S.
, p. 10573 - 10587 (2013/11/19)
This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.
Regioselectivity of selenium-mediated carbonylation of organolithium compounds with carbon monoxide
Fujiwara, Shin-Ichi,Nishiyama, Akira,Okada, Kazuhiro,Maeda, Hajime,Shin-Ike, Tsutomu,Sonoda, Noboru,Kambe, Nobuaki
experimental part, p. 1117 - 1123 (2010/08/19)
Regioselectivity of selenium-mediated carbonylation of organolithium compounds with carbon monoxide has been investigated. The reactions of lithium enolates of 2,2-dicyclohexyl aldehyde and 1,1-dicyclohexylpropane-2-one with selenium and carbon monoxide afforded the corresponding selenocarbonates by carbonylation at the enolate oxygen as the main product. Carbonylation of nitrogen-containing heterocycles can give either C- or N-carbonylation product, but diphenyl(4-pyridyno)methane, imidazole, and pyrazole afford only corresponding carbamoselenoates via N-carbonylation. Copyright Taylor & Francis Group.
