33566-59-5Relevant academic research and scientific papers
Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes
Kawamoto, Takuji,Uehara, Shohei,Hirao, Hidefumi,Fukuyama, Takahide,Matsubara, Hiroshi,Ryu, Ilhyong
, p. 3999 - 4007 (2014/05/20)
Cyanoborohydrides are efficient reagents in the reductive addition reactions of alkyl iodides and electron-deficient olefins. In contrast to using tin reagents, the reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine or carbon-chlorine bond. The reaction system was successfully applied to three-component reactions, including radical carbonylation. The rate constant for the hydrogen abstraction of a primary alkyl radical from tetrabutylammonium cyanoborohydride was estimated to be 4 M-1 s-1 at 25 °C by a kinetic competition method. This value is 3 orders of magnitude smaller than that of tributyltin hydride.
Tin-free giese reaction and the related radical carbonylation using Alkyl iodides and cyanoborohydrides
Ryu, Ilhyong,Uehara, Shohei,Hirao, Hidefumi,Fukuyama, Takahide
supporting information; experimental part, p. 1005 - 1008 (2009/04/07)
Tin-free Giese reaction and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. The reaction took place chemoselectively at the carbon-iodine bond but not at the carbon-bromine and carbon-chlorine bonds. The iodine atom transfer followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes
Benincori, Tiziana,Rizzo, Simona,Pilati, Tullio,Ponti, Alessandro,Sada, Mara,Pagliarini, Ella,Ratti, Simona,Giuseppe, Celentano,De Ferra, Lorenzo,Sannicolo, Franco
, p. 2289 - 2297 (2007/10/03)
A reliable methodology, applicable on a process-scale level, for producing enantiomerically pure chiral γ-lactones by enantioselective hydrogenation of γ-ketoesters, followed by cyclisation of the resulting γ-hydroxyesters, has been developed. The multi-step procedure was transformed into a one-pot reaction. A very efficient chiral Ru-complex, based on the biheteroaromatic diphosphine ligand tetraMe-BITIOP, was developed as a catalyst, capable of coupling fast kinetics with high stereoselection levels. Its structure was fully elucidated through 31P NMR, EPR and X-ray single-crystal analyses. The optimal experimental conditions are as follows: hydrogen pressure=30psi, S/C ratio=2000, 30% in weight substrate concentration. Yields are quantitative and enantiomeric excesses in the range 98-99.9%. Sensorial tests on the antipodes of two γ-lactones demonstrated the very different properties of the enantiomers.
A new convenient synthesis of methyl 4-oxoalkanoates
Kulinkovich,Sorokin
, p. 361 - 362 (2007/10/02)
Methyl 4-oxoalkanoates have been obtained in good yields by treatment of 1,2-dichloro-2-alken-4-ones with sodium carbonate in methanol followed by acid-catalyzed hydrolysis of the intermediate 5-alkyl-2,2-dimethoxy-2,3-dihydrofurans.
A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure
Gavin,Geraghty
, p. 1351 - 1361 (2007/10/02)
A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (+)-γ-jasmolactone as well as other naturally occurring lactones.
New Synthesis of (R)(+)-γ-Dodecanolide and (R)(+)-δ-Hexadecanolide
Jagadishwar Rao, Samala,Bhalerao, Uday T.,Tilak, Bal Dattatreya
, p. 257 - 258 (2007/10/02)
Total syntheses of (R)(+)-γ-dodecanolide (1), a sex pheromone of Rove beetles and (R)(+)-δ-hexadecanolide (2), a pheromone playing the role of queen substance of oriental hornet (Vespa orientalis) are described using thiophene as a chain extender.
Synthesis of Racemates and (+)-Enantiomers of γ-Caprolactone, γ-Dodecanolactone and δ-Hexadecanolactone, Lactonic Sex Pheromones of the Dermestid Beetle, Rove Beetle and Oriental Hornet
Naoshima, Yoshinobu,Ozawa, Hiroshi,Kondo, Hirokiyo,Hayashi, Shuichi
, p. 1431 - 1434 (2007/10/02)
A simple method based on regioselective two-step alkylation of easily-available diethyl 3-oxoglutarate (2) is described for the synthesis of racemates of the lactonic pheromones, 1a, 1b, and 1c.Their (+)-enantiomers were also synthesized by means of microbiological reduction of the intermediary keto acids.
Methyl 5-(Triphenylphosphoranylidene)levulinate: A Reagent for Homologation of Aldehydes to δ-Ene γ-Keto Esters
Ronald, Robert C.,Wheeler, Carl J.
, p. 138 - 139 (2007/10/02)
Methyl 5-(triphenylphosphoranylidene)levulinate has been synthesized and shown to condense with aldehydes to afford E δ-ene γ-keto esters in good yield.
Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives.
Smith,Lee,Gould,Cragoe Jr.
, p. 1292 - 1299 (2007/10/06)
A series of novel (8-aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids has been synthesized and evaluated for their ability to mimic the E series prostaglandins in stimulating cAMP formation in the mouse ovary and in binding to the rat kidney pl
