88098-04-8Relevant articles and documents
A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
Neuhaus, James D.,Bauer, Adriano,Pinto, Alexandre,Maulide, Nuno
, p. 16215 - 16218 (2018/11/23)
A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis
Amador, Adrian G.,Sherbrook, Evan M.,Lu, Zhan,Yoon, Tehshik P.
, p. 539 - 547 (2017/10/30)
A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions o
Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins
Kan, S. B. Jennifer,Maruyama, Hiroki,Akakura, Matsujiro,Kano, Taichi,Maruoka, Keiji
supporting information, p. 9487 - 9491 (2017/08/01)
A chiral-amine-catalyzed enantioselective and diastereodivergent method for aldehyde addition to electron-deficient olefins is presented. Hydrogen bonding was used as a control element to achieve unusual anti selectivity, which was further elucidated through mechanistic and computational studies.
Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones
Amador, Adrian G.,Sherbrook, Evan M.,Yoon, Tehshik P.
, p. 4722 - 4725 (2016/05/10)
Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.
Development of the Julia asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters
Kroutil, Wolfgang,Lasterra-Sanchez, M. Elena,Maddrell, Samuel J.,Mayon, Patrick,Morgan, Phillip,Roberts, Stanley M.,Thornton, Steven R.,Todd, Christine J.,Tueter, Melek
, p. 2837 - 2844 (2007/10/03)
Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4, 9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 ± 10 leucine residues.
Stereospecific Epoxidation of cis-2-Butene-1,4-diones to cis-2,3-Epoxybutane-1,4-diones with Oxodiperoxomolybdenum (VI), MoO5*H2O*HMPA
Chien, Chun-Sheng,Kawasaki, Tomomi,Sakamoto, Masanori,Tamura, Yasumitsu,Kita, Yasuyuki
, p. 2743 - 2749 (2007/10/02)
The epoxidation of cis-2-butene-1,4-diones 4 with (aqua)(hexamethylphosphoramide)oxodiperoxomolybdenum (VI), MoO5*H2O*HMPA, occured stereospecifically to give the cis-epoxides 5, whose stereochemistry was assigned on the basis of chemical evidence and a comparision of their spectral data with those of the corresponding trans-epoxides 6, which were prepared by the epoxidation of the trans-olefins 3 with alkaline hydrogen peroxide.
