17607-00-0Relevant academic research and scientific papers
SmI2-induced ring expansion reactions of alkyl (n+1)- oxobicyclo[n.1.0]alkane-1-carboxylates
Lee, Phil Ho,Lee, Jukyoung
, p. 7889 - 7892 (1998)
Alkyl 4-oxocycloalkanecarboxylates were prepared in good yield via ring expansion reactions of alkyl (n+1)-oxobicyclo[n.1.0]alkane-1-carboxylates mediated by SmI2-induced single electron transfer in THF/MeOH.
Dynamic Kinetic Sensitization of β-Dicarbonyl Compounds—Access to Medium-Sized Rings by De Mayo-Type Ring Expansion
Glorius, Frank,Guldi, Dirk M.,Henkel, Christian,James, Michael J.,Mai, Lukas A.,Paulisch, Tiffany O.,Strieth-Kalthoff, Felix
supporting information, (2021/12/27)
Herein, we present a photocatalyzed two-carbon ring expansion of β-dicarbonyl compounds with unactivated olefins that provides facile access to medium-sized rings. Selective sensitization of the substoichiometric enol tautomer enables reactivity of substr
Combined effects on selectivity in Fe-catalyzed methylene oxidation
Chen, Mark S.,White, M. Christina
scheme or table, p. 533 - 571 (2010/10/05)
Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.
Synthesis of linear and angular triquinane skeletons by O-stannyl ketyl-promoted fragmentation-cyclization reactions of α-keto cyclopropanes
Enholm, Eric J.,Jia, Zhaozhong J.
, p. 174 - 181 (2007/10/03)
Several investigations of rigid α-keto cyclopropane cleavage by O-stannyl ketyls are summarized herein. Tricyclo[3.3.0.02,8]octan-3-one ring systems were treated with nBu3SnH, which produced different ring-cleavage products depending on the location and type of substituent present. An examination of both radical-stabilizing substituents and stereoelectronic factors was initiated to understand what factors bias bond cleavage in a configurationally restricted α-ketocyclopropane via O-stannyl ketyls. A preference for cleavage of the cyclopropane bond with the best orbital overlap with the ketyl radical sp2-orbital even in the presence of radical stabilizing groups is indicated by these results. An O-stannyl ketyl ring scission-cyclization resulted in the novel synthesis of either a linear or an angular triquinane skeleton depending on the length and location an alkene tether on the tricyclo[3.3.0.02,8]octan-3-one precursor.
Ring Opening of Cyclopropylketones Induced by Photochemical Electron Transfer
Cossy, Janine,Furet, Nathalie,BouzBouz, Samir
, p. 11751 - 11764 (2007/10/02)
Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.
